Bicyclic compounds as pesticides

ABSTRACT

The present application relates to novel bicyclic compounds, to their use for controlling animal pests and to processes and intermediates for their preparation.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a § 371 National State Application ofPCT/EP2015/062211, filed Jun. 2, 2015, which claims priority to EuropeanApplication No. 14171338.8 filed Jun. 5, 2014.

BACKGROUND OF THE INVENTION Field of the Invention

The present application relates to novel bicyclic compounds, to theiruse for controlling animal pests and to processes and intermediates fortheir preparation.

Description of Related Art

WO 2012/102387 A1 describes heterocyclic compounds which can be usedparticularly as insecticides and acaricides.

WO 2003/033476 A1, WO 2004/014916 A1, WO 2008/152390, MedChemComm(2013), 4(2), 456-462, Bioorganic & Medicinal Chemistry Letters (2006),16(18), 4723-4727, Journal of the American Pharmaceutical Association(1912-1977) (1955), 44, 193-6 and Journal of the Chemical Society(1949), 1064-8 report on the synthesis and pharmacological properties ofcertain [1,3]thiazolo[4,5-d]pyrimidin-7(6H)-ones or[1,3]oxazolo[4,5-d]pyrimidin-7(6H)-ones.

Modern crop protection compositions have to meet many demands, forexample in relation to extent, persistence and spectrum of their actionand possible use. Questions of toxicity and of combinability with otheractive compounds or formulation auxiliaries play a role, as does thequestion of the expense that the synthesis of an active compoundrequires. In addition, resistances can occur. For all these reasonsalone, the search for novel crop protection compositions cannot beconsidered complete, and there is a constant need for novel compoundshaving improved properties compared to the known compounds, at least inrelation to individual aspects.

SUMMARY

It was an object of the present invention to provide compounds whichwiden the spectrum of the pesticides in various aspects.

This object, and further objects which are not stated explicitly but canbe discerned or derived from the connections discussed herein, areachieved by novel compounds of the formula (I)

in which

Het represents a radical from the group of

where the dotted line represents the bond to the carbon atom in theN═C-A group attached to Het and

-   -   G¹ represents N or C-A¹,    -   A¹ represents hydrogen, halogen, cyano, nitro, alkyl, haloalkyl,        alkoxy, haloalkoxy or in each case optionally substituted        cycloalkyl or cycloalkenyl,    -   A² represents hydrogen, halogen, cyano, nitro, alkyl, haloalkyl,        alkoxy, haloalkoxy or in each case optionally substituted        cycloalkyl or cycloalkenyl,    -   T represents oxygen or an electron pair,    -   R² represents hydrogen, alkyl, haloalkyl or optionally        substituted cycloalkyl,    -   R¹ represents a radical from the group consisting of hydrogen,        alkyl, haloalkyl, cyanoalkyl, alkenyl, haloalkenyl, alkynyl,        haloalkynyl, alkoxy, haloalkoxy, optionally halogen-substituted        alkoxyalkyl, optionally halogen-substituted bis(alkoxy)alkyl,        optionally halogen-substituted alkylsulphanylalkyl, optionally        halogen-substituted alkylcarbonylalkyl, optionally        halogen-substituted alkylsulphinylalkyl, optionally        halogen-substituted alkylsulphonylalkyl,        dialkylaminosulphanylalkyl, dialkylaminosulphinylalkyl,        dialkylaminosulphonylalkyl, optionally halogen-substituted        alkoxy carbonyl, optionally halogen-substituted        alkoxycarbonylalkyl, optionally halogen-substituted alkynyloxy,        optionally halogen-substituted alkynyloxycarbonyl,        dialkylaminocarbonyl, N-alkyl-N-cycloalkylaminocarbonyl,        dialkylaminocarbonylalkyl,        N-alkyl-N-cycloalkylaminocarbonylalkyl,        heterocyclylcarbonylalkyl, alkylsulphanyl, haloalkylsulphanyl,        alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl,        haloalkylsulphonyl, optionally halogen-, cyano-, nitro-, alkyl-,        cycloalkyl-, haloalkyl-, alkoxy-, haloalkoxy-, alkoxycarbonyl-,        haloalkoxycarbonyl- or hetaryl- (which for its part may        optionally be alkyl- or halogen-substituted) substituted        cycloalkyl, optionally halogen-, cyano-, nitro-, alkyl-,        haloalkyl-, cycloalkyl-, alkoxy-, haloalkoxy-, alkoxycarbonyl-,        haloalkoxycarbonyl- or hetaryl- (which for its part may        optionally be alkyl- or halogen-substituted) substituted        cycloalkylcarbonyl, optionally halogen-, cyano-, nitro-, alkyl-,        haloalkyl-, cycloalkyl-, alkoxy-, haloalkoxy-, alkoxycarbonyl-,        haloalkoxycarbonyl- or hetaryl- (which for its part may        optionally be alkyl- or halogen-substituted) substituted        cycloalkylalkyl, optionally substituted heterocyclyl, optionally        halogen-, cyano- (also in the alkyl part), nitro-, hydroxy-,        alkyl-, haloalkyl-, cycloalkyl- (which is optionally        substituted), alkoxy-, haloalkoxy-, alkylthio-, haloalkylthio-,        alkylsulphinyl-, alkylsulphonyl-, haloalkylsulphinyl-,        haloalkylsulphonyl-, amino-, alkylamino-, dialkylamino-,        alkylcarbonylamino-, alkoxycarbonylamino-, alkoxyalkyl-,        haloalkoxyalkyl-, alkenyl-, alkynyl-, cycloalkylalkyl-,        alkylcarbonyl-, alkoxycarbonyl- or aminocarbonyl-substituted        heterocyclylalkyl, optionally halogen-, cyano-, nitro-,        hydroxy-, amino-, alkyl-, haloalkyl-, cycloalkyl- (which is        optionally substituted) alkoxy- or haloalkoxy-substituted aryl,        optionally halogen-, cyano- (also in the alkyl part), nitro-,        hydroxy-, amino-, alkyl-, cycloalkyl- (which is optionally        substituted), haloalkyl-, alkoxy- or haloalkoxy-substituted        arylalkyl, optionally halogen-, cyano-, nitro-, hydroxy-,        alkyl-, haloalkyl-, cycloalkyl- (which is optionally        substituted), alkoxy-, haloalkoxy-, alkylthio-, haloalkylthio-,        alkylsulphinyl-, alkylsulphonyl-, haloalkylsulphinyl-,        haloalkylsulphonyl-, amino-, alkylamino-, dialkylamino-,        alkylaminocarbonyl-, dialkylaminocarbonyl-, alkylcarbonylamino-,        alkoxycarbonylamino-, alkoxyalkyl-, haloalkoxyalkyl-, alkenyl-,        alkynyl-, cycloalkylalkyl-, alkylcarbonyl-, alkoxycarbonyl- or        aminocarbonyl-substituted hetaryl, optionally halogen-, cyano-        (also in the alkyl part), nitro-, hydroxy-, alkyl-, haloalkyl-,        cycloalkyl- (which is optionally substituted), alkoxy-,        haloalkoxy-, alkylthio-, haloalkylthio-, alkylsulphinyl-,        alkylsulphonyl-, haloalkylsulphinyl-, haloalkylsulphonyl-,        amino-, alkylamino-, dialkylamino-, alkylcarbonylamino-,        alkoxycarbonylamino-, alkoxyalkyl-, haloalkoxyalkyl-, alkenyl-,        alkynyl-, cycloalkylalkyl-, alkylcarbonyl-, alkoxycarbonyl- or        aminocarbonyl-substituted hetarylalkyl,    -   R¹ also represents a radical from the group consisting of

-   -   -   in which the bond to the nitrogen atom in the C(═V)—N-Q            group in formula (I) is marked by the asterisk (*),

    -   R represents NR⁷R⁸, or represents an in each case optionally        substituted radical from the group consisting of alkyl, alkenyl,        alkynyl, alkoxyalkyl, alkyl-S(O)_(m), -alkyl, R⁷—CO-alkyl,        NR⁷R⁸—CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl,        cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl,        phenylalkyl, hetaryl and hetarylalkyl,

    -   W represents a radical from the group consisting of O, S, SO and        SO₂,

    -   X represents a radical from the group consisting of hydrogen,        halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy and        cycloalkyl,

    -   Y represents a radical from the group consisting of hydrogen,        halogen, alkyl, cycloalkyl, haloalkyl, alkoxy, haloalkoxy, cyano        and NR⁵R⁶,

    -   A represents oxygen or sulphur,

    -   Q represents nitrogen or C—R³ in which

    -   R³ represents a radical from the group consisting of hydrogen,        alkyl, cycloalkyl, haloalkyl, OH, alkoxy, haloalkoxy, SH,        alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, NH₂, alkylamino        and dialkylamino,

    -   V represents a radical from the group consisting of oxygen,        sulphur and NR⁴,

    -   R⁴ represents a radical from the group consisting of hydrogen,        cyano, alkyl, haloalkyl and cycloalkyl,

    -   R⁵ represents a radical from the group consisting of hydrogen,        alkyl, cycloalkyl and haloalkyl,

    -   R⁶ represents a radical from the group consisting of hydrogen,        alkyl, cycloalkyl and haloalkyl,

    -   or

    -   R⁵ and R⁶ together with the nitrogen to which they are bonded        represent an optionally substituted saturated or unsaturated 3-        to 6-membered ring which optionally contains one or more further        heteroatoms,

    -   R⁷ represents hydrogen, hydroxy or an in each case optionally        substituted radical from the group consisting of alkyl, alkoxy,        alkoxyalkyl, alkylcarbonyl, alkyl-S(O)_(m)-alkyl,        alkoxycarbonyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl,        cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl,        phenylalkyl, hetaryl and hetarylalkyl,

    -   R⁸ represents hydrogen, a metal ion, an optionally substituted        ammonium ion or an in each case optionally substituted radical        from the group consisting of alkyl, alkoxy, alkoxyalkyl,        alkyl-S(O)_(m)-alkyl and

    -   m represents a number from the group consisting of 0, 1 and 2.

Preferred substituents or ranges for the radicals shown in the compoundsof the formula (I) are elucidated below. The combination thereof formsthe range of preference (1).

Het represents a radical from the group consisting of

where the dotted line represents the bond to the carbon atom in theN═C-A group attached to Het.

-   -   G¹ represents N or C-A¹.    -   A¹ represents a radical from the group consisting of hydrogen,        halogen, C₁-C₆-alkyl and C₁-C₄-haloalkyl.    -   A² represents a radical from the group consisting of hydrogen,        halogen, C₁-C₆-alkyl and C₁-C₄-haloalkyl.    -   T represents oxygen or an electron pair.    -   R² represents a radical from the group consisting of hydrogen,        C₁-C₆-alkyl, C₁-C₆-haloalkyl and C₃-C₆-cycloalkyl which is        optionally mono- to trisubstituted by halogen, cyano, nitro,        C₁-C₃-alkyl, C₁-C₃-alkoxy and monosubstituted by        C₃-C₆-cycloalkyl.    -   R¹ represents a radical from the group consisting of hydrogen,        C₁-C₆-alkyl, C₂-C₆-haloalkyl, cyano-C₁-C₆-alkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, optionally halogen-substituted        C₁-C₆-alkoxy-C₁-C₆-alkyl, optionally halogen-substituted        bis(C₁-C₆-alkoxy)-C₁-C₆-alkyl, optionally halogen-substituted        C₁-C₆-alkylsulphanyl-C₁-C₆-alkyl, optionally halogen-substituted        C₁-C₄-alkylcarbonyl-C₁-C₄-alkyl, optionally halogen-substituted        C₁-C₆-alkylsulphinyl-C₁-C₆-alkyl, optionally halogen-substituted        C₁-C₆-alkylsulphonyl-C₁-C₆-alkyl,        di-(C₁-C₆-alkyl)-aminosulphanyl-C₁-C₆-alkyl,        di-(C₁-C₆)-alkylaminosulphinyl-C₁-C₆-alkyl,        di-(C₁-C₆-alkyl)-aminosulphonyl-C₁-C₆-alkyl, optionally        halogen-substituted C₁-C₆-alkoxycarbonyl, optionally        halogen-substituted C₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, optionally        halogen-substituted C₂-C₄-alkynyloxy, optionally        halogen-substituted C₂-C₄-alkynyloxycarbonyl,        di-(C₁-C₆-alkyl)-aminocarbonyl,        N—C₁-C₆-alkyl-N—C₃-C₆-cycloalkylaminocarbonyl,        di-(C₁-C₆-alkyl)-aminocarbonyl-C₁-C₆-alkyl,        N—C₁-C₆-alkyl-N—C₃-C₆-cycloalkylaminocarbonyl-C₁-C₆-alkyl,        heterocyclylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylsulphanyl,        C₁-C₆-haloalkylsulphanyl, C₁-C₆-alkylsulphinyl,        C₁-C₆-haloalkylsulphinyl, C₁-C₆-alkylsulphonyl,        C₁-C₆-haloalkylsulphonyl, optionally halogen-, cyano-, nitro-,        C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl-,        C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-, C₁-C₆-alkoxycarbonyl-,        C₁-C₆-haloalkoxycarbonyl- or hetaryl- (which for its part is        optionally C₁-C₆-alkyl- or halogen-substituted) substituted        C₃-C₆-cycloalkyl, optionally halogen-, cyano-, nitro-,        C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl-,        C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-, C₁-C₆-alkoxycarbonyl-,        C₁-C₆-haloalkoxycarbonyl- or hetaryl- (which for its part is        optionally C₁-C₆-alkyl- or halogen-substituted) substituted        C₃-C₆-cycloalkylcarbonyl, optionally halogen-, cyano-, nitro-,        C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl-,        C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-, C₁-C₆-alkoxycarbonyl-,        C₁-C₆-haloalkoxycarbonyl- or hetaryl- (which for its part is        optionally C₁-C₆-alkyl- or halogen-substituted) substituted        C₃-C₆-cycloalkyl-C₁-C₆-alkyl, optionally halogen-, cyano- (also        in the C₁-C₆-alkyl part of heterocyclyl-C₁-C₆-alkyl), nitro-,        hydroxy-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl-        (which is optionally substituted by halogen, cyano, C₁-C₆-alkyl        and C₃-C₆-cycloalkyl), C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-,        C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio-, C₁-C₆-alkylsulphinyl-,        C₁-C₆-alkylsulphonyl-, C₁-C₆-haloalkylsulphinyl-,        C₁-C₆-haloalkylsulphonyl-, amino-, C₁-C₆-alkylamino-,        di-(C₁-C₆-alkyl)-amino-, C₁-C₆-alkylcarbonylamino-, C₁-C₆-alkoxy        carbonylamino-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        C₁-C₆-haloalkoxy-C₁-C₆-alkyl-, C₂-C₆-alkenyl-, C₂-C₆-alkynyl-,        C₃-C₆-cycloalkyl-C₁-C₆-alkyl-, C₁-C₆-alkylcarbonyl-,        C₁-C₆-alkoxycarbonyl- or aminocarbonyl-substituted        heterocyclyl-C₁-C₆-alkyl, optionally halogen-, cyano-, nitro-,        hydroxy-, amino-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-,        C₃-C₆-cycloalkyl- (which is optionally substituted by halogen,        cyano, C₁-C₆-alkyl and C₃-C₆-cycloalkyl), C₁-C₆-alkoxy- or        C₁-C₆-haloalkoxy-substituted aryl, optionally halogen-, cyano-        (also in the C₁-C₆-alkyl part of aryl-C₁-C₆-alkyl), nitro-,        hydroxy-, amino-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-,        C₃-C₆-cycloalkyl- (which is optionally substituted by halogen,        cyano, C₁-C₆-alkyl and C₃-C₆-cycloalkyl), C₁-C₆-alkoxy- or        C₁-C₆-haloalkoxy-substituted aryl-C₁-C₆-alkyl, optionally        halogen-, cyano-, nitro-, hydroxy-, C₁-C₆-alkyl-,        C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl- (which is optionally        substituted by halogen, cyano, C₁-C₆-alkyl and        C₃-C₆-cycloalkyl), C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-,        C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio-, C₁-C₆-alkylsulphinyl-,        C₁-C₆-alkylsulphonyl-, C₁-C₆-haloalkylsulphinyl-,        C₁-C₆-haloalkylsulphonyl-, amino-, C₁-C₆-alkylamino-,        di-(C₁-C₆-alkyl)-amino-, C₁-C₆-alkylcarbonylamino-,        C₁-C₆-alkylaminocarbonyl-, di-(C₁-C₆-alkyl)-aminocarbonyl-,        C₁-C₆-alkoxycarbonylamino-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        C₁-C₆-haloalkoxy-C₁-C₆-alkyl-, C₂-C₆-alkenyl-, C₂-C₆-alkynyl-,        C₃-C₆-cycloalkyl-C₁-C₆-alkyl-, C₁-C₆-alkylcarbonyl-,        C₁-C₆-alkoxycarbonyl- or aminocarbonyl-substituted hetaryl,        optionally halogen-, cyano- (also in the C₁-C₆-alkyl part of        hetaryl-C₁-C₆-alkyl), nitro-, hydroxy-, C₁-C₆-alkyl-,        C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl- (which is optionally        substituted by halogen, cyano, C₁-C₆-alkyl and        C₃-C₆-cycloalkyl), C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-,        C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio-, C₁-C₆-alkylsulphinyl-,        C₁-C₆-alkylsulphonyl-, C₁-C₆-haloalkylsulphinyl-,        C₁-C₆-haloalkylsulphonyl-, amino-, C₁-C₆-alkylamino-,        di-(C₁-C₆-alkyl)-amino-, C₁-C₆-alkylcarbonylamino-,        C₁-C₆-alkoxycarbonylamino-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,        C₁-C₆-haloalkoxy-C₁-C₆-alkyl-, C₂-C₆-alkenyl-, C₂-C₆-alkynyl-,        C₃-C₆-cycloalkyl-C₁-C₆-alkyl-, C₁-C₆-alkylcarbonyl-,        C₁-C₆-alkoxycarbonyl- or aminocarbonyl-substituted        hetaryl-C₁-C₆-alkyl.    -   R¹ also represents a radical from the group consisting of

-   -   in which the bond to the nitrogen atom in the C(═V)—N-Q group in        formula (I) is marked by the asterisk (*).    -   R represents NR⁷R⁸ or represents in each case optionally        halogen-, oxygen- (leads to C═O) or cyano-substituted        C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl,        C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkyl-S(O)_(m)—C₁-C₄-alkyl,        represents R⁷—CO—C₁-C₄-alkyl, represents NR⁷R⁸—CO—C₁-C₄-alkyl,        represents C₃-C₆-cycloalkyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl, represents        C₃-C₆-cycloalkenyl which is optionally mono- or disubstituted by        oxygen (leads to C═O), C₁-C₄-alkyl, C₃-C₆-cycloalkyl,        C₁-C₄-alkoxy and C₁-C₄-haloalkyl, represents        C₃-C₆-cycloalkyl-C₁-C₄-alkyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl, represents        C₃-C₆-cycloalkenyl-C₁-C₄-alkyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl, represents        heterocyclyl which is optionally mono- or disubstituted by        oxygen (leads to C═O), C₁-C₄-alkyl, C₃-C₆-cycloalkyl,        C₁-C₄-alkoxy and C₁-C₄-haloalkyl, represents        heterocyclyl-C₁-C₄-alkyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl or represents        phenyl, phenyl-C₁-C₄-alkyl, hetaryl or hetaryl-C₁-C₄-alkyl, each        of which is optionally mono- to trisubstituted by halogen,        cyano, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.    -   W represents a radical from the group consisting of O, S, SO and        SO₂.    -   X represents a radical from the group consisting of hydrogen,        halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₃-C₆-cycloalkyl, C₁-C₆-alkoxy and C₁-C₆-haloalkoxy.    -   Y represents a radical from the group consisting of hydrogen,        halogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, cyano and NR⁵R⁶.    -   A represents sulphur.    -   Q represents nitrogen or C—R³.    -   R³ represents a radical from the group consisting of hydrogen,        C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, OH,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, SH, C₁-C₆-alkylsulphanyl,        C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl, NH₂,        C₁-C₆-alkylamino and di-(C₁-C₆-alkyl)-amino.    -   V represents a radical from the group consisting of oxygen,        sulphur and NR⁴.    -   R⁴ represents a radical from the group consisting of hydrogen,        cyano, C₁-C₆-alkyl, C₂-C₆-haloalkyl and C₃-C₆-cycloalkyl.    -   R⁵ represents a radical from the group consisting of hydrogen,        C₁-C₆-alkyl, C₃-C₆-cycloalkyl and C₂-C₆-haloalkyl.    -   R⁶ represents a radical from the group consisting of hydrogen,        C₁-C₆-alkyl, C₃-C₆-cycloalkyl and C₂-C₆-haloalkyl.    -   R⁵ and R⁶ together with the nitrogen atom to which they are        attached may also represent a saturated to triunsaturated 3- to        6-membered ring which is optionally substituted by halogen,        cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy, in particular aziridinyl, azirenyl,        diaziridinyl, diazirenyl, azetidinyl, dihydroazetyl,        diazetidinyl, dihydrodiazetyl, oxazetidinyl, oxazetyl,        thiazetidinyl, thiazetyl, pyrrolidinyl, dihydropyrrolyl,        pyrazolidinyl, dihydropyrazolyl, imidazolidinyl,        dihydroimidazolyl, oxazolidinyl, dihydrooxazolyl, thiazolidinyl,        dihydrothyazolyl, piperidinyl, piperazinyl,        hexahydropyridazinyl, hexahydropyrimidinyl, morpholinyl,        dioxazinanyl, thiomorpholine, dithiazinane, pyrrolyl, pyrazolyl,        imidazolyl, triazolyl and tetrazolyl.

R⁷ represents a radical from the group consisting of hydrogen, hydroxy,and C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₄-alkyl,C₁-C₆-alkyl-S(O)_(m)—C₁-C₄-alkyl, C₁-C₆-alkylcarbonyl,C₁-C₆-alkoxycarbonyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,C₃-C₆-cycloalkyl-C₁-C₃-alkyl, C₃-C₆-cycloalkenyl-C₁-C₃-alkyl,heterocyclyl, heterocyclyl-C₁-C₃-alkyl, each of which is optionallymono- or polysubstituted by halogen or mono- or disubstituted by cyano,and represents phenyl, phenyl-C₁-C₃-alkyl, hetaryl andhetaryl-C₁-C₃-alkyl, each of which is optionally mono- totetrasubstituted by C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₃-C₆-cycloalkyl, halogen or cyano.

-   -   R⁸ represents hydrogen, an alkali or alkaline earth metal ion,        or represents an ammonium ion which is optionally mono- to        tetrasubstituted by C₁-C₄-alkyl, or represents a radical from        the group consisting of C₁-C₄-alkyl, C₁-C₄-alkoxy,        C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₄-alkyl-S(O)_(m)—C₁-C₄-alkyl,        each of which is optionally mono- or polysubstituted by halogen        or mono- or disubstituted by cyano.    -   m represents a number from the group consisting of 0, 1 and 2.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

Particularly preferred substituents or ranges for the radicals shown inthe compounds of formula (I) are elucidated below. The combinationthereof forms the range of preference (2).

Het represents a radical from the group consisting of

where the dotted line represents the bond to the carbon atom in theN═C-A group attached to Het.

-   -   G¹ represents N or C-A¹.    -   A¹ represents a radical from the group consisting of hydrogen,        halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl.    -   A² represents a radical from the group consisting of hydrogen,        halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl.    -   T represents oxygen or an electron pair.    -   R¹ represents a radical from the group consisting of hydrogen,        C₁-C₄-alkyl, C₂-C₄-haloalkyl, cyano-C₁-C₄-alkyl, C₂-C₄-alkenyl,        C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, optionally halogen-substituted        C₁-C₂-alkoxy-C₁-C₄-alkyl, optionally halogen-substituted        bis(C₁-C₂-alkoxy)-C₁-C₄-alkyl, optionally halogen-substituted        C₁-C₄-alkylsulphanyl-C₁-C₄-alkyl, optionally halogen-substituted        C₁-C₄-alkylcarbonyl-C₁-C₄-alkyl, optionally halogen-substituted        C₁-C₄-alkylsulphinyl-C₁-C₄-alkyl, optionally halogen-substituted        C₁-C₄-alkylsulphonyl-C₁-C₄-alkyl,        di-(C₁-C₄-alkyl)-aminosulphanyl-C₁-C₄-alkyl,        di-(C₁-C₄-alkyl)-aminosulphinyl-C₁-C₄-alkyl,        di-(C₁-C₄-alkyl)-aminosulphonyl-C₁-C₄-alkyl, optionally        halogen-substituted C₁-C₄-alkoxycarbonyl, optionally        halogen-substituted C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, optionally        halogen-substituted C₂-C₄-alkynyloxy, optionally        halogen-substituted C₂-C₄-alkynyloxycarbonyl,        di-(C₁-C₄-alkyl)-aminocarbonyl, cycloalkylaminocarbonyl,        di-(C₁-C₄-alkyl)-aminocarbonyl-C₁-C₄-alkyl,        N—C₁-C₄-alkyl-N—C₃-C₆-cycloalkylaminocarbonyl-C₁-C₄-alkyl,        heterocyclylcarbonyl-C₁-C₄-alkyl, C₁-C₄-alkylsulphanyl,        C₁-C₄-haloalkylsulphanyl, C₁-C₄-alkylsulphinyl,        C₁-C₄-haloalkylsulphinyl, C₁-C₄-alkylsulphonyl,        C₁-C₄-haloalkylsulphonyl, optionally halogen-, cyano-, nitro-,        C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl-C₁-C₄-alkoxy-,        C₁-C₄-haloalkoxy-, C₁-C₄-alkoxycarbonyl-,        C₁-C₄-haloalkoxycarbonyl- or pyridyl- (which for its part is        optionally substituted by C₁-C₄-alkyl or halogen) substituted        C₃-C₆-cycloalkyl, optionally halogen-, cyano-, nitro-,        C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl-C₁-C₄-alkoxy-,        C₁-C₄-haloalkoxy-, C₁-C₄-alkoxycarbonyl-,        C₁-C₄-haloalkoxycarbonyl- or pyridyl- (which for its part is        optionally substituted by C₁-C₄-alkyl or halogen) substituted        C₃-C₆-cycloalkylcarbonyl, optionally halogen-, cyano-, nitro-,        C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl-C₁-C₄-alkoxy-,        C₁-C₄-haloalkoxy-, C₁-C₄-alkoxycarbonyl-,        C₁-C₄-haloalkoxycarbonyl-, pyridyl-, pyrimidyl-, pyrazanyl-,        pyridazinyl-, thiazolyl-, isothiazolyl-, thiadiazolyl-,        oxazolyl-, isoxazolyl-, oxadiazolyl-, pyrazolyl-, triazinyl- or        triazolyl- (where the hetaryls mentioned for their part are        optionally substituted by C₁-C₄-alkyl or halogen) substituted        C₃-C₆-cycloalkyl-C₁-C₄-alkyl, optionally halogen-, cyano- (also        in the C₁-C₄-alkyl part of heterocyclyl-C₁-C₄-alkyl), nitro-,        hydroxy-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl-        (which is optionally substituted by halogen, cyano, C₁-C₄-alkyl        and C₃-C₆-cycloalkyl), C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-,        C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulphinyl-,        C₁-C₄-alkylsulphonyl-, C₁-C₄-haloalkylsulphinyl-,        C₁-C₄-haloalkylsulphonyl-, amino, —C₁-C₄-alkylamino-,        di-(C₁-C₄-alkyl)-amino-, C₁-C₄-alkylcarbonylamino-,        C₁-C₄-alkoxycarbonylamino-, C₁-C₄-alkoxy-C₁-C₄-alkyl-,        C₁-C₄-haloalkoxy-C₁-C₄-alkyl-, C₂-C₄-alkenyl-, C₂-C₄-alkynyl-,        C₃-C₆-cycloalkyl-C₁-C₄-alkyl-, C₁-C₄-alkylcarbonyl-,        C₁-C₄-alkoxycarbonyl- or aminocarbonyl-substituted        heterocyclyl-C₁-C₄-alkyl, optionally halogen-, cyano-, nitro-,        hydroxy-, amino-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-,        C₃-C₆-cycloalkyl- (which is optionally substituted by halogen,        cyano, C₁-C₄-alkyl and C₃-C₆-cycloalkyl), C₁-C₄-alkoxy- or        C₁-C₄-haloalkoxy-substituted aryl, optionally halogen-, cyano-        (also in the C₁-C₄-alkyl part of aryl-C₁-C₄-alkyl), nitro-,        hydroxy-, amino-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-,        C₃-C₆-cycloalkyl- (which is optionally substituted by halogen,        cyano, C₁-C₄-alkyl and C₃-C₆-cycloalkyl), C₁-C₄-alkoxy- or        C₁-C₄-haloalkoxy-substituted aryl-C₁-C₄-alkyl, optionally        halogen-, cyano-, nitro-, hydroxy-, C₁-C₄-alkyl-,        C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl- (which is optionally        substituted by halogen, cyano, C₁-C₄-alkyl and        C₃-C₆-cycloalkyl), C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-,        C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulphinyl-,        C₁-C₄-alkylsulphonyl-, C₁-C₄-haloalkylsulphinyl-,        C₁-C₄-haloalkylsulphonyl-, amino-, C₁-C₄-alkylamino-,        di-(C₁-C₄-alkyl)-amino-, C₁-C₄-alkylcarbonylamino-,        C₁-C₄-alkylaminocarbonyl-, di-(C₁-C₄-alkyl)-aminocarbonyl-,        C₁-C₄-alkoxycarbonylamino-, C₁-C₄-alkoxy-C₁-C₄-alkyl-,        C₁-C₄-haloalkoxy-C₁-C₄-alkyl-, C₂-C₄-alkenyl-, C₂-C₄-alkynyl-,        C₃-C₆-cycloalkyl-C₁-C₄-alkyl-, C₁-C₄-alkylcarbonyl-,        C₁-C₄-alkoxycarbonyl- or aminocarbonyl-substituted hetaryl,        optionally halogen-, cyano- (also in the C₁-C₄-alkyl part of        hetaryl-C₁-C₄-alkyl), nitro-, hydroxy-, C₁-C₄-alkyl-,        C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl- (which is optionally        substituted by halogen, cyano, C₁-C₄-alkyl and        C₃-C₆-cycloalkyl), C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-,        C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulphinyl-,        C₁-C₄-alkylsulphonyl-, C₁-C₄-haloalkylsulphinyl-,        C₁-C₄-haloalkylsulphonyl-, amino-, C₁-C₄-alkylamino-,        C₁-C₄-alkylcarbonylamino-, C₁-C₄-alkoxycarbonylamino-,        C₁-C₄-alkoxy-C₁-C₄-alkyl-, C₁-C₄-haloalkoxy-C₁-C₄-alkyl-,        C₂-C₄-alkenyl-, C₂-C₄-alkynyl-, C₃-C₆-cycloalkyl-C₁-C₄-alkyl-,        C₁-C₄-alkylcarbonyl-, C₁-C₄-alkoxycarbonyl- or        aminocarbonyl-substituted hetaryl-C₁-C₄-alkyl.    -   R¹ also represents a radical from the group consisting of

-   -   -   in which the bond to the nitrogen atom in the C(═V)—N-Q            group in formula (I) is marked by the asterisk (*).

    -   R represents NR⁷R⁸ or represents C₁-C₆-alkyl, C₃-C₆-alkenyl,        C₃-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₃-alkyl,        C₁-C₄-alkyl-S(O)_(m)—C₁-C₃-alkyl, each of which is optionally        mono- to heptasubstituted by halogen, mono- or disubstituted by        oxygen (leads to C═O) or mono- or disubstituted by cyano,        represents R⁷—CO—C₁-C₂-alkyl, represents NR⁷R⁸—CO—C₁-C₂-alkyl,        represents C₃-C₈-cycloalkyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkyl, represents        C₃-C₈-cycloalkenyl which is optionally mono- or disubstituted by        oxygen (leads to C═O), C₁-C₄-alkyl, C₃-C₆-cycloalkyl,        C₁-C₄-alkoxy or C₁-C₄-haloalkyl, represents        C₃-C₆-cycloalkyl-C₁-C₄-alkyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkyl, represents        C₃-C₆-cycloalkenyl-C₁-C₄-alkyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkyl, represents        heterocyclyl which is optionally mono- or disubstituted by        oxygen (leads to C═O), C₁-C₄-alkyl, C₃-C₆-cycloalkyl,        C₁-C₄-alkoxy or C₁-C₄-haloalkyl, represents        heterocyclyl-C₁-C₄-alkyl which is optionally mono- or        disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,        C₃-C₆-cycloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkyl or represents        phenyl, phenyl-C₁-C₄-alkyl, hetaryl or hetaryl-C₁-C₄-alkyl, each        of which is optionally mono- to trisubstituted by halogen,        cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,        C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.

    -   W represents a radical from the group consisting of S, SO and        SO₂.

    -   X represents a radical from the group consisting of hydrogen,        fluorine, chlorine, bromine, iodine, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy.

    -   Y represents a radical from the group consisting of hydrogen,        fluorine, chlorine, bromine, iodine, cyano, C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and        C₁-C₄-haloalkoxy.

    -   A represents sulphur.

    -   Q represents nitrogen or C—R³.

    -   R³ represents a radical from the group consisting of hydrogen,        C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, OH,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, SH, C₁-C₄-alkylsulphanyl,        C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl, NH₂,        C₁-C₄-alkylamino and di-(C₁-C₄-alkyl)-amino.

    -   V represents oxygen.

    -   R⁷ represents a radical from the group consisting of hydrogen,        hydroxy, or C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₁-C₄-alkyl-S(O)_(m)—C₁-C₃-alkyl, C₁-C₄-alkylcarbonyl,        C₁-C₄-alkoxycarbonyl, C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkyl-C₁-C₃-alkyl, heterocyclyl and        heterocyclyl-C₁-C₃-alkyl, each of which is optionally mono- or        polysubstituted by halogen or mono- or disubstituted by cyano,        or represents phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl,        oxazolyl, pyrazolyl, thienyl, furanyl, pyridinylmethyl or        thiazolylmethyl, each of which is optionally mono- to        trisubstituted by C₁-C₄-alkyl, C₁-C₃-haloalkyl, C₁-C₃-alkoxy,        C₁-C₃-haloalkoxy, cyclopropyl, fluorine, chlorine, bromine or        cyano.

    -   R⁸ represents hydrogen, represents an alkali or alkaline earth        metal ion, or represents an ammonium ion which is optionally        mono- to tetrasubstituted by C₁-C₄-alkyl, or represents a        radical from the group consisting of C₁-C₄-alkyl, C₁-C₄-alkoxy,        C₁-C₄-alkoxy-C₁-C₂-alkyl and C₁-C₄-alkyl-S(O)_(m)—C₁-C₂-alkyl,        each of which is optionally mono- or polysubstituted by halogen        or mono- or disubstituted by cyano.

    -   m represents a number from the group consisting of 0, 1 and 2.

Very particularly preferred substituents or ranges of the radicals shownin the compounds of the formula (I) are elucidated below. Thecombination thereof forms the range of preference (3).

Het represents a radical from the group consisting of

where the dotted line represents the bond to the carbon atom in theN═C-A group attached to Het.

-   -   G¹ represents N or C-A¹.    -   A¹ represents a radical from the group consisting of hydrogen,        fluorine and chlorine.    -   T represents oxygen or an electron pair.    -   R¹ represents a radical from the group consisting of methyl,        ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl,        tert-butyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl,        2,2-difluoro-n-propyl, methylsulphanylmethyl,        methylsulphanylethyl, methylsulphanyl-n-propyl,        trifluoromethylsulphonylmethyl, ethylsulphonylmethyl,        2,2,2-trifluoroethylsulphonylmethyl,        2,2-difluoroethylsulphonylmethyl, isopropylsulphanylmethyl,        methylsulphinylmethyl, trifluoromethylsulphinylmethyl,        ethylsulphinylmethyl, 2,2,2-trifluoroethylsulphinylmethyl,        2,2-difluoroethylsulphinylmethyl, isopropylsulphinylmethyl,        methylsulphonylmethyl, trifluoromethylsulphonylmethyl,        ethylsulphonylmethyl, 2,2,2-trifluoroethylsulphonylmethyl,        2,2-difluoroethylsulphonylmethyl, isopropylsulphonylmethyl,        methoxy carbonyl, ethoxy carbonyl, methoxycarbonylmethyl,        ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl,        dimethylaminocarbonyl, diethylaminocarbonyl,        N-ethyl-N-methylaminocarbonyl,        N-isopropyl-N-methylaminocarbonyl, dimethylaminocarbonylmethyl,        diethylaminocarbonylmethyl, N-ethyl-N-methylaminocarbonylmethyl,        N-isopropyl-N-methylaminocarbonylmethyl,        dimethylaminocarbonylethyl, diethylaminocarbonylethyl,        N-ethyl-N-methylaminocarbonylethyl,        N-isopropyl-N-methylaminocarbonylethyl,        N-cyclopropyl-N-methylaminocarbonylmethyl,        N-cyclopropyl-N-methylaminocarbonylethyl, methylsulphanyl,        trifluoromethylsulphanyl, ethylsulphanyl,        2,2,2-trifluoroethylsulphanyl, 2,2-difluoroethylsulphanyl,        isopropylsulphanyl, methylsulphinyl, trifluoromethylsulphinyl,        ethylsulphinyl, 2,2,2-trifluoroethylsulphinyl,        2,2-difluoroethylsulphinyl, isopropylsulphinyl, methylsulphonyl,        trifluoromethylsulphonyl, ethylsulphonyl,        2,2,2-trifluoroethylsulphonyl, 2,2-difluoroethylsulphonyl,        isopropylsulphonyl, cyclopropyl, 1-cyanocyclopropyl,        1-chlorocyclopropyl, 1-fluorocyclopropyl, 2-cyanocyclopropyl,        2-chlorocyclopropyl, 2-fluorocyclopropyl, 2,2,3,3-tetrafluorocy        clopropyl, 2-cyclopropylcyclopropyl, cyclobutyl, cyclopentyl,        cyclohexyl, 4-trifluoromethylcyclohexyl, cyclopropylmethyl,        cyclopropylethyl, cyclobutylmethyl,        N-cyclopropyl-N-methylaminocarbonyl,        morpholin-4-ylcarbonylmethyl, piperazin-1-ylcarbonylmethyl,        4-methylpiperazin-1-ylcarbonylmethyl, of heterocyclylmethyl and        heterocyclylethyl, each of which is optionally mono-, di- or        trisubstituted by identical or different substitutents from the        group consisting of fluorine, chlorine, bromine, cyano, nitro,        hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl,        trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy and        difluoromethoxy, of in each case cyclopropyl-substituted        heterocyclylmethyl and heterocyclylethyl, where the cyclopropyl        radical is optionally mono- or disubstituted by methyl,        fluorine, chlorine, cyano or monosubstituted by cyclopropyl, of        hetaryl which is optionally mono- or disubstituted by identical        or different substituents from the group consisting of fluorine,        chlorine, bromine, cyano, nitro, hydroxy, amino, methyl, ethyl,        isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy,        trifluoromethoxy, difluoromethoxy, dimethylaminocarbonyl, of        hetaryl substituted by cyclopropyl, where the cyclopropyl        radical is optionally mono- or disubstituted by methyl,        fluorine, chlorine, cyano or monosubstituted by cyclopropyl, of        aryl which is optionally mono-, di- or trisubstituted by        identical or different substituents from the group consisting of        fluorine, chlorine, bromine, cyano, nitro, hydroxy, amino,        methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl,        difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy and        trifluoroethoxy, of aryl substituted by cyclopropyl, where the        cyclopropyl radical is optionally mono- or disubstituted by        methyl, fluorine, chlorine, cyano or monosubstituted by        cyclopropyl, of arylmethyl and arylethyl, each of which is        optionally mono-, di- or trisubstituted by identical or        different substituents from the group consisting of fluorine,        chlorine, bromine, cyano, nitro, hydroxy, amino, methyl, ethyl,        isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy,        trifluoromethoxy, difluoromethoxy, of arylmethyl and arylethyl        in each case substituted by cyclopropyl, where the cyclopropyl        radical is optionally mono- or disubstituted by methyl,        fluorine, chlorine, cyano or monosubstituted by cyclopropyl, of        hetarylmethyl and hetarylethyl, each of which is optionally        mono- or disubstituted by identical or different substituents        from the group consisting of fluorine, chlorine, bromine, cyano,        nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl,        trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy,        difluoromethoxy, of hetarylmethyl and hetarylethyl in each case        substituted by cyclopropyl, where the cyclopropyl radical is        optionally mono- or disubstituted by methyl, fluorine, chlorine,        cyano or monosubstituted by cyclopropyl.    -   R¹ also represents a radical from the group consisting of

-   -   -   in which the bond to the nitrogen atom in the C(═V)—N-Q            group in formula (I) is marked by the asterisk (*).

    -   R represents NR⁷R⁸ or represents a radical from the group        consisting of C₁-C₄-alkyl, C₃-C₄-alkenyl, C₃-C₄-alkynyl,        C₁-C₂-alkoxy-C₁-C₂-alkyl and C₁-C₂-alkyl-S(O)_(m)—C₁-C₂-alkyl,        each of which is optionally mono-, di-, tri-, tetra- or        pentasubstituted by fluorine, chlorine or mono- or disubstituted        by cyano, represents R⁷—CO—C₁-C₂-alkyl, represents        NR⁷R⁸—CO—C₁-C₂-alkyl, represents C₃-C₆-cycloalkyl which is        optionally mono- or disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy        or C₁-C₂-haloalkyl or by an oxygen atom (leads to C═O),        represents C₃-C₆-cycloalkenyl which is optionally mono- or        disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy or C₁-C₂-haloalkyl or        by an oxygen atom (leads to C═O), represents        C₃-C₆-cycloalkyl-C₁-C₂-alkyl which is optionally mono- or        disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy or C₁-C₂-haloalkyl,        represents C₃-C₆-cycloalkenyl-C₁-C₂-alkyl which is optionally        mono- or disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy or        C₁-C₂-haloalkyl, represents heterocyclyl which is optionally        mono- or disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy or        C₁-C₂-haloalkyl, represents heterocyclyl-C₁-C₂-alkyl which is        optionally mono- or disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy        or C₁-C₂-haloalkyl or represents phenyl, benzyl, pyridyl,        pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, furanyl,        pyridinylmethyl or thiazolylmethyl, each of which is optionally        mono- or disubstituted by fluorine, chlorine, bromine, cyano,        methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy,        difluoromethoxy or trifluoromethoxy.

    -   W represents a radical from the group consisting of S, SO and        SO₂.

    -   X represents a radical from the group consisting of hydrogen,        fluorine, chlorine, bromine, cyano, methyl, ethyl,        trifluoromethyl, methoxy, ethoxy, difluoromethoxy and        trifluoromethoxy.

    -   Y represents a radical from the group consisting of hydrogen,        fluorine, chlorine, bromine, cyano, methyl, ethyl,        trifluoromethyl, methoxy, ethoxy, difluoromethoxy and        trifluoromethoxy.

    -   A represents sulphur.

    -   Q represents nitrogen or C—R³.

    -   R³ represents hydrogen.

    -   V represents oxygen.

    -   R⁷ represents a radical from the group consisting of hydrogen,        hydroxy, or represents C₁-C₄-alkyl, C₁-C₄-alkoxy,        C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkyl-S(O)_(m)—C₁-C₂-alkyl,        C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₃-C₆-cycloalkyl,        C₃-C₆-cycloalkyl-C₁-C₃-alkyl, heterocyclyl or        heterocyclyl-C₁-C₃-alkyl, each of which is optionally mono-,        di-, tri-, tetra- or pentasubstituted by fluorine, chlorine or        mono- or disubstituted by cyano, or represents phenyl, benzyl,        pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl,        furanyl, pyridinylmethyl or thiazolylmethyl, each of which is        optionally mono- to trisubstituted by C₁-C₄-alkyl,        C₁-C₃-haloalkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, cyclopropyl,        fluorine, chlorine, bromine or cyano.

    -   R⁸ represents hydrogen, an alkali or alkaline-earth metal ion,        an ammonium ion which is optionally mono- to tetrasubstituted by        C₁-C₄-alkyl, or represents a radical from the group consisting        of C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₂-alkyl and        C₁-C₄-alkyl-S(O)_(m)—C₁-C₂-alkyl, each of which is optionally        mono-, di-, tri-, tetra- or pentasubstituted by fluorine,        chlorine or is mono- or disubstituted by cyano.

    -   m represents a number from the group consisting of 0, 1 and 2.

Especially preferred substituents or ranges for the radicals shown inthe compounds of formula (I) are elucidated below. The combinationthereof forms the range of preference (4).

Het represents a radical from the group consisting of

where the dotted line represents the bond to the carbon atom in theN═C-A group attached to Het.

-   -   G¹ represents N or C-A¹.    -   A¹ represents a radical from the group consisting of hydrogen,        fluorine and chlorine.    -   T represents oxygen or an electron pair.    -   R¹ represents a radical from the group consisting of methyl,        ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl,        tert-butyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl,        2,2-difluoro-n-propyl, methylsulphanylmethyl,        methylsulphanylethyl, methylsulphanyl-n-propyl,        trifluoromethylsulphonylmethyl, ethylsulphonylmethyl,        2,2,2-trifluoroethylsulphonylmethyl,        2,2-difluoroethylsulphonylmethyl, isopropylsulphanylmethyl,        methylsulphinylmethyl, trifluoromethylsulphinylmethyl,        ethylsulphinylmethyl, 2,2,2-trifluoroethylsulphinylmethyl,        2,2-difluoroethylsulphinylmethyl, isopropylsulphinylmethyl,        methylsulphonylmethyl, trifluoromethylsulphonylmethyl,        ethylsulphonylmethyl, 2,2,2-trifluoroethylsulphonylmethyl,        2,2-difluoroethylsulphonylmethyl, isopropylsulphonylmethyl,        methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl,        ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl,        dimethylaminocarbonyl, diethylaminocarbonyl,        N-ethyl-N-methylaminocarbonyl,        N-isopropyl-N-methylaminocarbonyl, dimethylaminocarbonylmethyl,        diethylaminocarbonylmethyl, N-ethyl-N-methylaminocarbonylmethyl,        N-isopropyl-N-methylaminocarbonylmethyl,        dimethylaminocarbonylethyl, diethylaminocarbonylethyl,        N-ethyl-N-methylaminocarbonylethyl,        N-isopropyl-N-methylaminocarbonylethyl,        N-cyclopropyl-N-methylaminocarbonylmethyl,        N-cyclopropyl-N-methylaminocarbonylethyl, methylsulphanyl,        trifluoromethylsulphanyl, ethylsulphanyl,        2,2,2-trifluoroethylsulphanyl, 2,2-difluoroethylsulphanyl,        isopropylsulphanyl, methylsulphinyl, trifluoromethylsulphinyl,        ethylsulphinyl, 2,2,2-trifluoroethylsulphinyl,        2,2-difluoroethylsulphinyl, isopropylsulphinyl, methylsulphonyl,        trifluoromethylsulphonyl, ethylsulphonyl,        2,2,2-trifluoroethylsulphonyl, 2,2-difluoroethylsulphonyl,        isopropylsulphonyl, cyclopropyl, 1-cyanocyclopropyl,        1-chlorocyclopropyl, 1-fluorocyclopropyl, 2-cyanocyclopropyl,        2-chlorocyclopropyl, 2-fluorocyclopropyl,        2,2,3,3-tetrafluorocyclopropyl, 2-cyclopropylcyclopropyl,        cyclobutyl, cyclopentyl, cyclohexyl,        4-trifluoromethylcyclohexyl, cyclopropylmethyl,        cyclopropylethyl, cyclobutylmethyl,        N-cyclopropyl-N-methylaminocarbonyl,        morpholin-4-ylcarbonylmethyl, piperazin-1-ylcarbonylmethyl,        4-methylpiperazin-1-ylcarbonylmethyl,    -   of heterocyclylmethyl and heterocyclylethyl, each of which is        optionally mono-, di- or trisubstituted by identical or        different substitutents from the group consisting of fluorine,        chlorine, bromine, cyano, nitro, hydroxy, amino, methyl, ethyl,        isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy,        trifluoromethoxy and difluoromethoxy, of in each case        cyclopropyl-substituted heterocyclylmethyl and        heterocyclylethyl, where the cyclopropyl radical is optionally        mono- or disubstituted by methyl, fluorine, chlorine, cyano or        monosubstituted by cyclopropyl, of hetaryl which is optionally        mono- or disubstituted by identical or different substituents        from the group consisting of fluorine, chlorine, bromine, cyano,        nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl,        trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy,        difluoromethoxy, dimethylaminocarbonyl, of hetaryl substituted        by cyclopropyl, where the cyclopropyl radical is optionally        mono- or disubstituted by methyl, fluorine, chlorine, cyano or        monosubstituted by cyclopropyl, of aryl which is optionally        mono-, di- or trisubstituted by identical or different        substituents from the group consisting of fluorine, chlorine,        bromine, cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl,        tert-butyl, trifluoromethyl, difluoromethyl, methoxy,        trifluoromethoxy, difluoromethoxy and trifluoroethoxy, of aryl        substituted by cyclopropyl, where the cyclopropyl radical is        optionally mono- or disubstituted by methyl, fluorine, chlorine,        cyano or monosubstituted by cyclopropyl, of arylmethyl and        arylethyl, each of which is optionally mono-, di- or        trisubstituted by identical or different substituents from the        group consisting of fluorine, chlorine, bromine, cyano, nitro,        hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl,        trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy,        difluoromethoxy, of arylmethyl and arylethyl in each case        substituted by cyclopropyl, where the cyclopropyl radical is        optionally mono- or disubstituted by methyl, fluorine, chlorine,        cyano or monosubstituted by cyclopropyl, of hetarylmethyl and        hetarylethyl, each of which is optionally mono- or disubstituted        by identical or different substituents from the group consisting        of fluorine, chlorine, bromine, cyano, nitro, hydroxy, amino,        methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl,        difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, of        hetarylmethyl and hetarylethyl in each case substituted by        cyclopropyl, where the cyclopropyl radical is optionally mono-        or disubstituted by methyl, fluorine, chlorine, cyano or        monosubstituted by cyclopropyl.    -   R¹ also represents the radical of the formula

-   -   -   in which the bond to the nitrogen atom in the C(═V)—N-Q            group in formula (I) is marked by the asterisk (*).

    -   R represents methyl, ethyl, propyl, isopropyl, n-butyl,        isobutyl, sec-butyl, tert-butyl, allyl, 2-butenyl, propargyl,        2-butynyl, each of which is optionally mono-, di- or        trisubstituted by fluorine or monosubstituted by cyano, or        represents C₃-C₆-cycloalkyl which is optionally monosubstituted        by methyl, ethyl, methoxy, ethoxy or trifluoromethyl, or        represents C₃-C₆-cycloalkylmethyl which is optionally        monosubstituted by methyl, ethyl, methoxy or trifluoromethyl, or        represents phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl and        pyridinylmethyl, each of which is optionally mono- or        disubstituted by fluorine, chlorine, bromine, cyano, methyl,        ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl,        methoxy, ethoxy, difluoromethoxy or trifluoromethoxy.

    -   W represents a radical from the group consisting of S, SO and        SO₂.

    -   X represents a radical from the group consisting of hydrogen,        fluorine, chlorine, bromine, cyano, methyl, ethyl,        trifluoromethyl, methoxy, ethoxy, difluoromethoxy and        trifluoromethoxy.

    -   Y represents a radical from the group consisting of hydrogen,        fluorine, chlorine, bromine, cyano, methyl, ethyl,        trifluoromethyl, methoxy, ethoxy, difluoromethoxy and        trifluoromethoxy.

    -   A represents sulphur.

    -   Q represents nitrogen or C—R³.

    -   R³ represents hydrogen or methyl.

    -   V represents oxygen.

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which the substituents have the meanings below. Thecombination thereof forms the range of preference (5).

-   -   Het represents

where the dotted line represents the bond to the carbon atom in theN═C-A group attached to Het.

-   -   G¹ represents C-A¹.    -   A¹ represents hydrogen.    -   T represents oxygen or an electron pair.    -   R¹ represents        -   methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl,            sec-butyl, tert-butyl, 2,2,2-trifluoroethyl,            2,2-difluoroethyl, 2,2-difluoro-n-propyl,            dimethylaminocarbonyl, diethylaminocarbonyl,            N-ethyl-N-methylaminocarbonyl,            N-isopropyl-N-methylaminocarbonyl,            dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl,            N-ethyl-N-methylaminocarbonylmethyl,            N-isopropyl-N-methylaminocarbonylmethyl,            dimethylaminocarbonylethyl, diethylaminocarbonylethyl,            N-ethyl-N-methylaminocarbonylethyl,            N-isopropyl-N-methylaminocarbonylethyl,            N-cyclopropyl-N-methylaminocarbonylmethyl,            N-cyclopropyl-N-methylaminocarbonylethyl, cyclopropyl,            cyclobutyl, cyclopentyl, cyclohexyl, represents            hetarylmethyl or hetarylethyl, each of which is optionally            mono- or disubstituted by identical or different            substituents from the group consisting of fluorine,            chlorine, bromine, cyano, nitro, hydroxy, amino, methyl,            ethyl, isopropyl, tert-butyl, trifluoromethyl,            difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy.    -   R¹ also represents

-   -   -   in which the bond to the nitrogen atom in the C(═V)—N-Q            group in formula (I) is marked by the asterisk (*).

    -   R represents C₁-C₄-alkyl which is optionally mono- to        trisubstituted by fluorine or chlorine.

    -   W represents a radical from the group consisting of S and SO.

    -   X represents a radical from the group consisting of hydrogen,        fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl and        trifluoromethyl.

    -   Y represents a radical from the group consisting of hydrogen,        fluorine, chlorine, bromine, iodine (in particular fluorine),        methyl and ethyl.

    -   A represents sulphur.

    -   Q represents nitrogen or C—R³.

    -   R³ represents hydrogen.

    -   V represents oxygen.

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which the substituents have the meanings below. Thecombination thereof forms the range of preference (6).

-   -   Het represents

where the dotted line represents the bond to the carbon atom in theN═C-A group attached to Het.

-   -   G¹ represents C-A¹ or N.    -   A¹ represents hydrogen or fluorine.    -   T represents oxygen or an electron pair.    -   R¹ represents        -   methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl,            sec-butyl, tert-butyl, 2,2,2-trifluoroethyl,            2,2-difluoroethyl, 2,2-difluoro-n-propyl,            dimethylaminocarbonyl, diethylaminocarbonyl,            N-ethyl-N-methylaminocarbonyl,            N-isopropyl-N-methylaminocarbonyl,            dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl,            N-ethyl-N-methylaminocarbonylmethyl,            N-isopropyl-N-methylaminocarbonylmethyl,            dimethylaminocarbonylethyl, diethylaminocarbonylethyl,            N-ethyl-N-methylaminocarbonylethyl,            N-isopropyl-N-methylaminocarbonylethyl,            N-cyclopropyl-N-methylaminocarbonylmethyl,            N-cyclopropyl-N-methylaminocarbonylethyl, cyclopropyl,            cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,            optionally dimethylaminocarbonyl-substituted benzothienyl,            optionally halogen-, methyl- or trifluoroethoxy-substituted            phenyl, optionally methyl-, methoxy-, difluoromethoxy- or            halogen-substituted phenylmethyl, represents hetarylmethyl            or hetarylethyl, each of which is optionally mono- or            disubstituted by identical or different substituents from            the group consisting of fluorine, chlorine, bromine, cyano,            nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl,            trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy,            difluoromethoxy.    -   R¹ also represents

-   -   -   in which the bond to the nitrogen atom in the C(═V)—N-Q            group in formula (I) is marked by the asterisk (*).

    -   R represents C₁-C₄-alkyl which is optionally mono- to        trisubstituted by fluorine or chlorine.

    -   W represents a radical from the group consisting of S, SO and        SO₂.

    -   X represents a radical from the group consisting of hydrogen,        fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl and        trifluoromethyl.

    -   Y represents a radical from the group consisting of hydrogen,        fluorine, chlorine, bromine, iodine (in particular fluorine),        methyl and ethyl.

    -   A represents sulphur.

    -   Q represents nitrogen or C—R³.

    -   R³ represents hydrogen or methyl.

    -   V represents oxygen.

In the preferred definitions, whose combination forms the range ofpreference (1), unless stated otherwise,

alkali metal ion is selected from the group consisting of lithium,sodium, potassium, rubidium, caesium, preferably from the groupconsisting of lithium, sodium and potassium,

alkaline earth metal ion is selected from the group consisting ofberyllium, magnesium, calcium, strontium, barium, preferably from thegroup consisting of magnesium and calcium,

halogen is selected from the group consisting of fluorine, chlorine,bromine and iodine, preferably in turn from the group consisting offluorine, chlorine and bromine,

aryl (including as part of a larger unit, for example arylalkyl) isselected from the group consisting of phenyl, naphthyl, anthryl,phenanthrenyl, and represents preferably in turn phenyl,

hetaryl (synonymous with heteroaryl, including as part of a larger unit,for example hetarylalkyl) is selected from the group consisting offuryl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl,1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl,pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, benzofuryl, benzoisofuryl, benzothienyl,benzoisothienyl, indolyl, isoindolyl, indazolyl, benzothiazolyl,benzoisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl,2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl, cinnolinyl,phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl,benzotriazinyl, purinyl, pteridinyl and indolizinyl,

heterocyclyl represents a saturated 4-, 5- or 6-membered ring containing1 or 2 nitrogen atoms and/or one oxygen atom and/or one sulphur atom,for example azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl,oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, tetrahydrofuryl,piperazinyl, morpholinyl.

In the particularly preferred definitions whose combination forms therange of preference (2), unless stated otherwise,

alkali metal ion is selected from the group consisting of lithium,sodium, potassium, rubidium, caesium, preferably from the groupconsisting of lithium, sodium and potassium,

alkaline earth metal ion is selected from the group consisting ofberyllium, magnesium, calcium, strontium, barium, preferably from thegroup consisting of magnesium and calcium,

halogen is selected from the group consisting of fluorine, chlorine,bromine and iodine, preferably in turn from the group consisting offluorine, chlorine and bromine,

aryl (including as part of a larger unit, for example arylalkyl) isselected from the group of phenyl, naphthyl, anthryl and phenanthrenyl,and is preferably in turn phenyl,

hetaryl (synonymous with heteroaryl, also as part of a larger unit suchas, for example, hetarylalkyl) is selected from the group consisting ofpyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl,isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyrimidinyl, pyridazinyl,pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl,benzothienyl,

heterocyclyl is selected from the group consisting of azetidinyl,azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl,thiolanyl, thianyl, tetrahydrofuryl, piperazinyl, morpholinyl.

In the very particularly preferred definitions and the especiallypreferred definitions whose combination forms the range of preference(3) and the range of preference (4), respectively, unless statedotherwise,

alkali metal ion represents an ion from the group consisting of lithium,sodium, potassium, rubidium, caesium, preferably from the groupconsisting of lithium, sodium, potassium,

alkaline earth metal ion represents an ion from the group consisting ofberyllium, magnesium, calcium, strontium and barium, preferably from thegroup consisting of magnesium and calcium,

halogen represents fluorine, chlorine, bromine and iodine, preferably inturn fluorine, chlorine and bromine,

heterocyclyl represents a radical from the group consisting of oxetanyl,thiethanyl, tetrahydrofuryl and morpholinyl, aryl represents phenyl and

hetaryl (synonymous with heteroaryl, including as part of a larger unitsuch as, for example, hetarylalkyl) represents a radical from the groupconsisting of pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, thiazolyl,pyrazolyl and benzothienyl.

In the definitions which form the range of preference (5) and the rangeof preference (6),

halogen represents fluorine, chlorine, bromine and iodine, preferably inturn fluorine, chlorine and bromine, and

hetaryl represents pyridyl, pyrimidinyl, thiazolyl, pyrazolyl andbenzothienyl.

Halogen-substituted radicals, for example haloalkyl, are mono- orpolyhalogenated, up to the maximum number of possible substituents. Inthe case of polyhalogenation, the halogen atoms can be identical ordifferent. In this case, halogen represents fluorine, chlorine, bromineor iodine, especially fluorine, chlorine or bromine

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,may each be straight-chain or branched if possible, including incombination with heteroatoms, as, for example, in alkoxy.

Unless stated otherwise, optionally substituted radicals may be mono- orpolysubstituted, where the substituents in the case of poly substitutionmay be the same or different.

If T in the radical Het of the formula

represents an electron pair, the radical is present as a pyridinederivative of the formula

If T in the radical Het of the formula

represents oxygen, the radical is present as a pyridine N-oxidederivative of the formula

Here, the formal charges (+ at nitrogen and − at oxygen) were omittedfrom the illustration (however, cf. Example 24 in Table 1).

The radical definitions or elucidations given above in general terms orwithin areas of preference apply to the end products and correspondinglyto the starting materials and intermediates. These radical definitionscan be combined with one another as desired, i.e. including combinationsbetween the respective ranges of preference.

According to the invention, preference is given to compounds of theformula (I) which contain a combination of the definitions listed aboveas being preferred (range of preference (1)).

According to the invention, particular preference is given to compoundsof the formula (I) which contain a combination of the definitions listedabove as being particularly preferred (range of preference (2)).

According to the invention, very particular preference is given tocompounds of the formula (I) which contain a combination of thedefinitions listed above as being very particularly preferred (range ofpreference (3)).

According to the invention, special preference is given to compounds ofthe formula (I) which contain a combination of the definitions listedabove as being especially preferred (range of preference (4)).

A further group of compounds of the formula (I) which are emphasized arethose which form the range of preference (5).

A further group of compounds of the formula (I) which are emphasized arethose which form the range of preference (6).

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which Het represents the radical of the formula

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which Het represents pyridin-3-yl.

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which Het represents 5-fluoropyridin-3-yl.

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which Het represents pyrimidin-5-yl.

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which Het represents pyridazin-4-yl.

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which R′ represents the radical

A further preferred embodiment of the invention relates to compounds ofthe formula (I) in which Q represents C—H.

The compounds of the formula (I) may possibly also, depending on thenature of the substituents, be in the form of stereoisomers, i.e. in theform of geometric and/or optical isomers or isomer mixtures of varyingcomposition. This invention provides both the pure stereoisomers and anydesired mixtures of these isomers, even though it is generally onlycompounds of the formula (I) that are discussed here.

However, preference is given in accordance with the invention to usingthe optically active, stereoisomeric forms of the compounds of theformula (I) and salts thereof.

The invention therefore relates both to the pure enantiomers anddiastereomers and to mixtures thereof for controlling animal pests,including arthropods and particularly insects.

It has additionally been found that the novel compounds of the formula(I) can be prepared by the processes described below.

The compounds of the formula (I) can be prepared, for example, byprocess A in two steps, as shown in the scheme below. The aminothiazolesof the formula (III) required for this purpose can be prepared, forexample, by process B from the heteroarylthioamides.

The compounds of the formula (II) also form part of the subject-matterof the invention and can be prepared as described in the processesbelow.

where Het, Q and R¹ have the meanings given above and R¹ representshydrogen or alkyl (in particular methyl and ethyl).

Process A

The compounds of the formula (I) can be synthesized in two steps usingmethods known from the literature.

In the first synthesis step, compounds of the formula (III) can beconverted by various methods into carboxamides of the formula (II). WhenR′=alkyl, this conversion can take place without activation (cf. B. M.Trost and I. Fleming in Comprehensive Organic Synthesis, Ed. Pergamon,1991, Vol. 6). As an alternative, the literature discloses activationmethods by formation of an aluminium amide (see T. Ooi and K. Marouka inScience of Synthesis, Ed. Georg Thieme, 2003, Vol. 7, 225-246). Thesealuminium amides can be prepared, for example from the amines or saltsthereof by reaction with trimethylaluminium or their air-stable adductwith 1,4-diazobicyclo[2.2.3]octane (DABCO) (cf. S. Woodward in Tet.Lett. 2006, 47, 5767-5769).

As an alternative, the aminothiazoles of the formula (III) whereR′=alkyl can be converted in two stages to the amides of the formulae(II): first hydrolysis to give the carboxylates, for example by reactionwith an inorganic base (preferably sodium hydroxide and potassiumhydroxide solutions), optionally with an inert organic solvent,optionally it is possible by acidification with a diluted acid (forexample aqueous hydrochloric acid) to prepare and isolate the carboxylicacids of the formula (III) where R′=hydrogen; subsequent amidationreaction with the desired amines leads to the compounds of the formula(II). A number of reaction conditions have been described for theamidation step, for example G. Benz in Comprehensive Organic Synthesis,1^(st) Ed., Pergamon Press, Oxford, 1991, Vol. 6, pp. 381-417; P. D.Bailey et al. in Comprehensive Organic Functional Group Transformation,1st Ed., Elsevier Science Ltd., Oxford, 1995, Vol. 5, pp. 257-308 and R.C. Larock in Comprehensive Organic Transformations, 2nd Ed., Wiley-VCH,New York, Weinheim, 1999, pp. 1929-1994. Some of these reactions proceedvia intermediate carbonyl chlorides, which can be used in isolated formor having been generated in situ.

The amidation reactions are optionally effected in the presence of acondensing agent, optionally in the presence of an acid acceptor andoptionally in the presence of a solvent.

Useful condensing agents are all the condensing agents typically usablefor such amidation reactions. Examples include acid halide formers suchas phosgene, phosphorus trichloride, oxalyl chloride or thionylchloride; carbodiimides such as N,N′-dicyclohexylcarbodiimide (DCC) and1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI), or other customarycondensing agents such as phosphorus pentoxide, polyphosphoric acid,N,N′-carbonyldiimidazole, 2-chloropyridine 1-methiodide (Mukaiyama'sreagent), 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ),triphenylphosphine/carbon tetrachloride, bromotripyrrolidinophosphoniumhexafluorophosphate (BROP),O-(1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphoniumhexafluorophosphate (BOP), N,N,N′,N′-bis(tetramethylene)chlorouroniumtetrafluoroborate, O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HBTU), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-bis(tetramethylene)uronium hexafluorophosphate,O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate(TBTU), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-bis(tetramethylene)uroniumtetrafluoroborate,O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU), 1-hydroxybenzotriazole (HOBt) and4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium salt (DMT.MM),usually available as the chloride. These reagents can be used separatelyor, if appropriate, in combination.

Useful acid acceptors are all customary inorganic or organic bases, forexample triethylamine, diisopropylethylamine, N-methylmorpholine orN,N-dimethylaminopyridine. Process A according to the invention isoptionally carried out in the presence of a suitable reaction auxiliary,for example N,N-dimethylformamide or N,N-dimethylaminopyridine. Usefulsolvents or diluents include all inert organic solvents, for examplealiphatic or aromatic hydrocarbons (such as petroleum ether, toluene),halogenated hydrocarbons (such as chlorotoluene, dichloromethane,chloroform, 1,2-dichloroethane), ethers (such as diethyl ether, dioxane,tetrahydrofuran, 1,2-dimethoxyethane), esters (such as ethyl or methylacetate), nitrohydrocarbons (such as nitromethane, nitroethane,nitrobenzene), nitriles (such as acetonitrile, benzonitrile), amides(such as N,N-dimethylformamide, N,N-dimethylacetamide,N-methylformanilide, N-methylpyrrolidone, hexamethylphosphortriamide),and also dimethyl sulphoxide or water or mixtures of the solventsmentioned.

It is also possible to use mixed anhydrides for the preparation ofcompounds of the formula (III) (cf. J. Am. Chem. Soc. 1967, 5012). Inthis process, it is possible to use various chloroformic esters, forexample isobutyl chloroformate and isopropyl chloroformate. It islikewise possible to use diethylacetyl chloride, trimethylacetylchloride and the like for this purpose.

In a second synthesis step, the carboxamides of the formula (II) can becyclized to the compounds of the formula (I).

In the case that Q=C—R³ in which R³ is H or alkyl, the cyclization ofcarboxamides of the formula (II) can be performed with an orthoester,such as triethyl orthoformate or triethyl orthoacetate, optionally inthe presence of a solvent or diluent (for example in the presence ofalcohols such as ethanol, but also in the presence ofN,N-dimethylformamide or N,N-dimethylacetamide), optionally in thepresence of an organic acid (for example para-toluenesulphonic acid oracetic acid) or inorganic acid (for example hydrochloric acid orsulphuric acid) in catalytic or stoichiometric amounts or in excess. Theacids mentioned can also be used in place of the solvent or diluent. Inthe case that R³═H there are examples of such reactions with triethylorthoformate in Archiv der Pharmazie 2000, 333(8), 261-266 (for thepreparation of quinazolinones), J. Het. Chem. 1990, 27(7), 1953-1956(idem.), WO2010/54398 (for the preparation of pyrazinopyrimidinones). Inthe case that R³=methyl, see, for example, WO2010/100189 (forpreparation of quinazolinones).

In the case that Q=C—R³, in which R³ represents alkyl or haloalkyl, thethiazolopyrimidinones of the formula (I) can also be prepared byreaction of the carboxamides of the formula (II) with appropriatecarbonyl halides or carboxylic anhydrides by methods known from theliterature, such as described, for example, in WO2009/143049 in the casethat R³=methyl and in WO 2008/039489 in the case thatR³=trifluoromethyl.

In the case that Q+N, the thiazolopyrimidinones of the formula (I) canbe prepared by azodiazotization of the carboxamides of the formula (II)according to methods known from the literature. For example, compoundsof the formula (II) are treated at 0 to 5° C. with a nitrite source,such as sodium nitrite or isobutyl nitrite, typically in water, alcoholor a polar inert solvent, and in the presence of an organic or inorganicacid. Examples of reaction conditions can be found in WO 2004/242572 orin J. Amer. Chem. Soc. Perkin Trans. 1, 1980, 633-638).

The compounds of the formula (II)/(III) are novel and also form part ofthe subject matter of the invention.

General Processes for the Oxidation of Thioethers to Sulphoxides andSulphones

Compounds of the formula (I) in which W represents SO (sulphoxides) or Wrepresents SO₂ (sulphones) can be prepared by oxidation by processesknown from the literature from compounds of the formula (I) in which Wrepresents S (thioethers), for example by an oxidizing agent in asuitable solvent or diluent. Suitable oxidizing agents are, for example,diluted nitric acid, hydrogen peroxide, Oxone® and peroxycarboxylicacids, for example meta-chloroperbenzoic acid. Suitable solvents ordiluents are inert organic solvents, typically acetonitrile andhalogenated solvents such as dichloromethane, chloroform ordichloroethane, and water and alcohols such as methanol for the reactionwith Oxone®.

It is also possible to introduce suitable anilines R¹—NH₂, halidesR¹-hal or boronic acids R¹—B(OH)₂, in which W represents SO or SO₂, byprocess A-1 or A-2. These can be oxidized from the correspondingprecursors in which W represents S by processes known from theliterature, such as, for example, those described in WO 2013/092350.

A large number of different methods are suitable for generatingenantiomerically enriched sulphoxides, as described by A. R. Maguire inARKIVOC, 2011 (i), 1-110: metal-catalysed asymmetric oxidations ofthioethers, for example with titanium or vanadium as the most frequentlyemployed catalyst sources, in the form of Ti(O^(i)Pr₄) or VO(acac)₂,together with a chiral ligand and an oxidizing agent such as tert-butylhydroperoxide (TBHP), 2-phenylpropan-2-yl hydroperoxide (CHP) orhydrogen peroxide; non-metal-catalysed asymmetric oxidations employingchiral oxidizing agents or chiral catalysts; electrochemical orbiological asymmetric oxidations and also kinetic resolution ofsulphoxides and nucleophilic shift (according to Andersen's method).

The enantiomers can also be obtained from the racemate, for example bypreparative separation by means of a chiral HPLC.

The aminothiazoles of the formula (III) required in process A can beprepared, for example, by process B. In the case of not commerciallyavailable heteroarylthioamides as starting materials for process B,these can be prepared in a known manner by process C1 or C2:

Process C1

Heteroarylthioamides of the formula (VII) can be prepared in one step bymethods known in principle from the corresponding commercially availableheteroarylcarboxamides of the formula (VIII) and suitable sulphurdonors. Thus, WO 2013/104415 by Petterson et al. describes a method fortransforming carbonyl groups into thiocarbonyl groups by reacting thecorresponding starting materials at a temperature between 50° C. and100° C. with a suitable sulphur compound, for example diphosphoruspentasulphide-dipyridine complex, optionally in an inert organic solvent(e.g. acetonitrile).

Process C2

As an alternative to process B1, heteroarylthioamides of the formula(VII) can be prepared in one step by methods known in principle from thecorresponding commercially available heteroarylnitriles of the formula(IX) and suitable sulphur donors. For example according to Mahammed etal. (Journal of Sulfur Chemistry, 28(3), 233-237; 2007) by reaction withthioacetic acid in the presence of calcium hydride at a temperaturebetween 50° C. and 100° C. in a solvent-free environment. An alternativemicrowave-supported synthesis, for example, has also been described(Synlett, (14), 2615-2617; 2004) where the corresponding nitriles arereacted at a temperature between 50° C. and 100° C. with ammoniumsulphide in an inert organic solvent (e.g. alcohols).

Process B

Examples of the conversion of thioamides into thiazole derivatives oftype (VI) are described in WO 2013/092711 A1 (cf. also Bioorganic &Medicinal Chemistry Letters (2010), 20(9), 2828-2831). The thioamides(VII), which are commercially available or can be prepared according toprocess C1 or C2, are initially reacted in a suitable inert solvent(e.g. dioxane or toluene) under reflux temperature, optionally in thepresence of a base (e.g. pyridine) with dimethyl 2-chloromalonate ordimethyl 2-bromomalonate to give the desired compound (VI).

The preparation of the compound (V) is then carried out (for exampleaccording to Bioorganic & Medicinal Chemistry Letters (2010), 20(9),2828-2831) by reacting (VI) with trifluoromethanesulphonic anhyride inthe presence of a suitable base (e.g. triethylamine, sodium carbonate,pyridine or lutidine) in an inert solvent (e.g. dichloromethane) at atemperature between −20° C. and room temperature.

It is known that compounds of type (V) can be transformed (for exampleaccording to WO 2003/101985 A1) into compounds of type (IV) by heatingwith benzylamines in inert solvents (e.g. dioxane) at temperaturesbetween 50 and 100° C.

Removal of the benzylamine function for preparing the target compoundsof type (III) can be carried out by methods known in principle (forexample WO 2003/066629 A2) by heating in suitable acids (e.g.trifluoroacetic acid or sulphuric acid) at temperatures between 20 and80° C. Any acid amides formed in this reaction are hydrolyzed by heatingwith potassium carbonate in a water/methanol mixture to afford thetarget compound (III).

The thiazole derivatives of the formulae (VI) to (III) prepared in thisway can be separated, for example by chromatographic separation onsilica gel or RP(C-18), or by trituration or recrystallization usingsuitable solvents.

Isomers

Depending on the nature of the substituents, the compounds of theformula (I) may be in the form of geometric and/or optically activeisomers or corresponding isomer mixtures in different compositions.These stereoisomers are, for example, enantiomers, diastereomers,atropisomers or geometric isomers. The invention thus encompasses purestereoisomers and any desired mixtures of these isomers.

Methods and Uses

The invention also relates to methods for controlling animal pests, inwhich compounds of the formula (I) are allowed to act on animal pestsand/or their habitat. The control of the animal pests is preferablyconducted in agriculture and forestry, and in material protection.Preferably excluded from this are methods for the surgical ortherapeutic treatment of the human or animal body and diagnostic methodscarried out on the human or animal body.

The invention further relates to the use of the compounds of the formula(I) as pesticides, especially crop protection agents.

In the context of the present application, the term “pesticide” in eachcase also always comprises the term “crop protection agent”.

The compounds of the formula (I), given good plant tolerance, favourabletoxicity to warm-blooded species and good environmental compatibility,are suitable for protecting plants and plant organs against biotic andabiotic stress factors, for increasing harvest yields, for improving thequality of the harvested material and for controlling animal pests,especially insects, arachnids, helminths, nematodes and molluscs, whichare encountered in agriculture, in horticulture, in animal husbandry, inaquatic cultures, in forests, in gardens and leisure facilities, in theprotection of stored products and of materials, and in the hygienesector. They can preferably be used as pesticides. They are effectiveagainst normally sensitive and resistant species and against all or somestages of development. The abovementioned pests include:

pests from the phylum of the Arthropoda, especially from the class ofthe Arachnida, for example Acarus spp., for example Acarus siro, Aceriakuko, Aceria sheldoni, Aculops spp., Aculus spp., for example Aculusfockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychusviennensis, Argas spp., Boophilus spp., Brevipalpus spp., for exampleBrevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroidesspp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoidespteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychusspp., for example Eotetranychus hicoriae, Epitrimerus pyri,Eutetranychus spp., for example Eutetranychus banksi, Eriophyes spp.,for example Eriophyes pyri, Glycyphagus domesticus, Halotydeusdestructor, Hemitarsonemus spp., for example Hemitarsonemus latus(=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectusspp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp.,Oligonychus spp., for example Oligonychus coniferarum, Oligonychusilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychuspratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp.,Ornithonyssus spp., Panonychus spp., for example Panonychus citri(=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi),Phyllocoptruta oleivora, Platytetranychus multidigituli,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemusspp., Steneotarsonemus spinki, Tarsonemus spp., for example Tarsonemusconfusus, Tarsonemus pallidus, Tetranychus spp., for example Tetranychuscanadensis, Tetranychus cinnabarinus, Tetranychus turkestani,Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasateslycopersici;

from the class of the Chilopoda, for example Geophilus spp., Scutigeraspp.;

from the order or the class of the Collembola, for example Onychiurusarmatus; Sminthurus viridis;

from the class of the Diplopoda, for example Blaniulus guttulatus;

from the class of the Insecta, for example from the order of theBlattodea, for example Blatta orientalis, Blattella asahinai, Blattellagermanica, Leucophaea maderae, Panchlora spp., Parcoblatta spp.,Periplaneta spp., for example Periplaneta americana, Periplanetaaustralasiae, Supella longipalpa;

from the order of the Coleoptera, for example Acalymma vittatum,Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp.,for example Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus,Amphimallon solstitialis, Anobium punctatum, Anoplophora spp.,Anthonomus spp., for example Anthonomus grandis, Anthrenus spp., Apionspp., Apogonia spp., Atomaria spp., for example Atomaria linearis,Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp.,for example Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotomatrifurcata, Ceutorrhynchus spp., for example Ceutorrhynchus assimilis,Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., forexample Chaetocnema confinis, Chaetocnema denticulata, Chaetocnemaectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., for exampleCosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculiospp., for example Curculio caryae, Curculio caryatrypes, Curculioobtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus,Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturusspp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestesspp., Diabrotica spp., for example Diabrotica balteata, Diabroticabarberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctataundecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgiferazeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epilachnaspp., for example Epilachna borealis, Epilachna varivestis, Epitrixspp., for example Epitrix cucumeris, Epitrix fuscula, Epitrixhirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp.,Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychusarator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hyperapostica, Hypomeces squamosus, Hypothenemus spp., for exampleHypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens,Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae,Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp.,for example Leucoptera coffeella, Lissorhoptrus oryzophilus, Lixus spp.,Luperomorpha xanthodera, Luperodes spp., Lyctus spp., Megascelis spp.,Melanotus spp., for example Melanotus longulus oregonensis, Meligethesaeneus, Melolontha spp., for example Melolontha melolontha, Migdolusspp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Niptushololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagusoryzae, Otiorhynchus spp., for example Otiorhynchus cribricollis,Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchusrugosostriarus, Otiorhynchus sulcatus, Oxycetonia jucunda, Phaedoncochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp.,for example Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotretaramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp.,Prostephanus truncatus, Psylliodes spp., for example Psylliodes affinis,Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobiusventralis, Rhizopertha dominica, Sitophilus spp., for example Sitophilusgranarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais,Sphenophorus spp., Stegobium paniceum, Sternechus spp., for exampleSternechus paludatus, Symphyletes spp., Tanymecus spp., for exampleTanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebriomolitor, Tenebrioides mauretanicus, Tribolium spp., for exampleTribolium audax, Tribolium castaneum, Tribolium confusum, Trogodermaspp., Tychius spp., Xylotrechus spp., Zabrus spp., for example Zabrustenebrioides;

from the order of the Diptera, for example, Aedes spp., for exampleAedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyzaspp., for example Agromyza frontella, Agromyza parvicornis, Anastrephaspp., Anopheles spp., for example Anopheles quadrimaculatus, Anophelesgambiae, Asphondylia spp., Bactrocera spp., for example Bactroceracucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus,Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata,Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis,Cochliomya spp., Contarinia spp., for example Contarinia johnsoni,Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi,Contarinia sorghicola, Contarinia tritici, Cordylobia anthropophaga,Cricotopus sylvestris, Culex spp., for example Culex pipiens, Culexquinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacusoleae, Dasineura spp., for example Dasineura brassicae, Delia spp., forexample Delia antiqua, Delia coarctata, Delia florilega, Delia platura,Delia radicum, Dermatobia hominis, Drosophila spp., for exampleDrosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Fanniaspp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrelliaspp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp.,Liriomyza spp., for example Liriomyza brassicae, Liriomyza huidobrensis,Liriomyza sativae, Lucilia spp., for example Lucilia cuprina, Lutzomyiaspp., Mansonia spp., Musca spp., for example Musca domestica, Muscadomestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp.,Paralauterborniella subcincta, Pegomya spp., for example Pegomya betae,Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp.,Phormia spp., Piophila casei, Prodiplosis spp., Psila rosae, Rhagoletisspp., for example Rhagoletis cingulata, Rhagoletis completa, Rhagoletisfausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella,Sarcophaga spp., Simulium spp., for example Simulium meridionale,Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., for exampleTipula paludosa, Tipula simplex;

from the order of the Hemiptera, for example Acizzia acaciaebaileyanae,Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiponspp., for example Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp.,Agonoscena spp., Aleyrodes proletella, Aleurolobus barodensis,Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., forexample Amrasca bigutulla, Amrasca devastans, Anuraphis cardui,Aonidiella spp., for example Aonidiella aurantii, Aonidiella citrina,Aonidiella inornata, Aphanostigma piri, Aphis spp., for example Aphiscitricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines,Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni,Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphisviburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp.,Aspidiotus spp., for example Aspidiotus nerii, Atanus spp., Aulacorthumsolani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspismelaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicorynebrassicae, Cacopsylla spp., for example Cacopsylla pyricola, Calligyponamarginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae,Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis,Chlorita onukii, Chondracris rosea, Chromaphis juglandicola,Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp.,for example Coccus hesperidum, Coccus longulus, Coccuspseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp.,Ctenarytaina spp., Dalbulus spp., Dialeurodes citri, Diaphorina citri,Diaspis spp., Drosicha spp., Dysaphis spp., for example Dysaphisapiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp.,Empoasca spp., for example Empoasca abrupta, Empoasca fabae, Empoascamaligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., for exampleEriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneuraspp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisiaspp., Geococcus coffeae, Glycaspis spp., Heteropsylla cubana,Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis,Hyalopterus pruni, Icerya spp., for example Icerya purchasi, Idiocerusspp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., forexample Lecanium corni (=Parthenolecanium corni), Lepidosaphes spp., forexample Lepidosaphes ulmi, Lipaphis erysimi, Lycorma delicatula,Macrosiphum spp., for example Macrosiphum euphorbiae, Macrosiphum lilii,Macrosiphum rosae, Macrosteles facifrons, Mahanarva spp., Melanaphissacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum,Monellia costalis, Monelliopsis pecanis, Myzus spp., for example Myzusascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzuspersicae, Myzus nicotianae, Nasonovia ribisnigri, Nephotettix spp., forexample Nephotettix cincticeps, Nephotettix nigropictus, Nilaparvatalugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis,Pachypsylla spp., Parabemisia myricae, Paratrioza spp., for exampleParatrioza cockerelli, Parlatoria spp., Pemphigus spp., for examplePemphigus bursarius, Pemphigus populivenae, Peregrinus maidis,Phenacoccus spp., for example Phenacoccus madeirensis, Phloeomyzuspasserinii, Phorodon humuli, Phylloxera spp., for example Phylloxeradevastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcusspp., for example Planococcus citri, Prosopidopsylla flava,Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcusspp., for example Pseudococcus calceolariae, Pseudococcus comstocki,Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni,Psyllopsis spp., Psylla spp., for example Psylla buxi, Psylla mali,Psylla pyri, Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., forexample Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis,Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp.,Rhopalosiphum spp., for example Rhopalosiphum maidis, Rhopalosiphumoxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetiaspp., for example Saissetia coffeae, Saissetia miranda, Saissetianeglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum,Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatellafurcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae,Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae,Tomaspis spp., Toxoptera spp., for example Toxoptera aurantii, Toxopteracitricidus, Trialeurodes vaporariorum, Trioza spp., for example Triozadiospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.;

from the suborder of the Heteroptera, for example Anasa tristis,Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylommalivida, Cavelerius spp., Cimex spp., for example Cimex adjunctus, Cimexhemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp.,Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocorishewetti, Dysdercus spp., Euschistus spp., for example Euschistus heros,Euschistus servus, Euschistus tristigmus, Euschistus variolarius,Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horciasnobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossusoccidentalis, Leptoglossus phyllopus, Lygocoris spp., for exampleLygocoris pabulinus, Lygus spp., for example Lygus elisus, Lygushesperus, Lygus lineolaris, Macropes excavatus, Monalonion atratum,Nezara spp., for example Nezara viridula, Oebalus spp., Piesma quadrata,Piezodorus spp., for example Piezodorus guildinii, Psallus spp.,Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoriscastanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.;

from the order of the Hymenoptera, for example Acromyrmex spp., Athaliaspp., for example Athalia rosae, Atta spp., Diprion spp., for exampleDiprion similis, Hoplocampa spp., for example Hoplocampa cookei,Hoplocampa testudinea, Lasius spp., Linepithema humile, Monomoriumpharaonis, Sirex spp., Solenopsis invicta, Tapinoma spp., Urocerus spp.,Vespa spp., for example Vespa crabro, Xeris spp.;

from the order of the Isopoda, for example Armadillidium vulgare,Oniscus asellus, Porcellio scaber;

from the order of the Isoptera, for example Coptotermes spp., forexample Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp.,Incisitermes spp., Microtermes obesi, Odontotermes spp., Reticulitermesspp., for example Reticulitermes flavipes, Reticulitermes hesperus;

from the order of the Lepidoptera, for example Achroia grisella,Acronicta major, Adoxophyes spp., for example Adoxophyes orana, Aedialeucomelas, Agrotis spp., for example Agrotis segetum, Agrotis ipsilon,Alabama spp., for example Alabama argillacea, Amyelois transitella,Anarsia spp., Anticarsia spp., for example Anticarsia gemmatalis,Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrixthurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp.,Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposinaniponensis, Cheimatobia brumata, Chilo spp., for example Chiloplejadellus, Chilo suppressalis, Choristoneura spp., Clysia ambiguella,Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp.,Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., forexample Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphaniaspp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium,Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., for exampleEphestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyaspostvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctisspp., for example Euproctis chrysorrhoea, Euxoa spp., Feltia spp.,Galleria mellonella, Gracillaria spp., Grapholitha spp., for exampleGrapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpaspp., for example Helicoverpa armigera, Helicoverpa zea, Heliothis spp.,for example Heliothis virescens, Hofmannophila pseudospretella,Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoriaflavofasciata, Laphygma spp., Leucinodes orbonalis, Leucoptera spp., forexample Leucoptera coffeella, Lithocolletis spp., for exampleLithocolletis blancardella, Lithophane antennata, Lobesia spp., forexample Lobesia botrana, Loxagrotis albicosta, Lymantria spp., forexample Lymantria dispar, Lyonetia spp., for example Lyonetia clerkella,Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitisleda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogoncloacellus, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp.,Ostrinia spp., for example Ostrinia nubilalis, Oulema melanopus, Oulemaoryzae, Panolis flammea, Parnara spp., Pectinophora spp., for examplePectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., forexample Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycterspp., for example Phyllonorycter blancardella, Phyllonoryctercrataegella, Pieris spp., for example Pieris rapae, Platynota stultana,Plodia interpunctella, Plusia spp., Plutella xylostella (=Plutellamaculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletiaspp., for example Pseudaletia unipuncta, Pseudoplusia includens,Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., for exampleSchoenobius bipunctifer, Scirpophaga spp., for example Scirpophagainnotata, Scotia segetum, Sesamia spp., for example Sesamia inferens,Sparganothis spp., Spodoptera spp., for example Spodoptera eradiana,Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica,Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Teciasolanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella,Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusiaspp., for example Trichoplusia ni, Tryporyza incertulas, Tuta absoluta,Virachola spp.;

from the order of the Orthoptera or Saltatoria, for example Achetadomesticus, Dichroplus spp., Gryllotalpa spp., for example Gryllotalpagryllotalpa, Hieroglyphus spp., Locusta spp., for example Locustamigratoria, Melanoplus spp., for example Melanoplus devastator,Paratlanticus ussuriensis, Schistocerca gregaria;

from the order of the Phthiraptera, for example Damalinia spp.,Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxeravastatrix, Phthirus pubis, Trichodectes spp.;

from the order of the Psocoptera, for example Lepinotus spp., Liposcelisspp.;

from the order of the Siphonaptera, for example Ceratophyllus spp.,Ctenocephalides spp., for example Ctenocephalides canis, Ctenocephalidesfelis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis;

from the order of the Thysanoptera, for example Anaphothrips obscurus,Baliothrips biformis, Drepanothrips reuteri, Enneothrips flavens,Frankliniella spp., for example Frankliniella fusca, Frankliniellaoccidentalis, Frankliniella schultzei, Frankliniella tritici,Frankliniella vaccinii, Frankliniella williamsi, Heliothrips spp.,Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp.,Taeniothrips cardamomi, Thrips spp., for example Thrips palmi, Thripstabaci;

from the order of the Zygentoma (=Thysanura), for example Ctenolepismaspp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;

from the class of the Symphyla, for example Scutigerella spp., forexample Scutigerella immaculata;

pests from the phylum of the Mollusca, in particular from the class ofthe Bivalvia, for example Dreissena spp.;

and also from the class of the Gastropoda, for example Anion spp., forexample Anion ater rufus, Biomphalaria spp., Bulinus spp., Derocerasspp., for example Deroceras laeve, Galba spp., Lymnaea spp., Oncomelaniaspp., Pomacea spp., Succinea spp.;

animal and human parasites from the phyla of the Platyhelminthes andNematoda, for example Aelurostrongylus spp., Amidostomum spp.,Ancylostoma spp., Angiostrongylus spp., Anisakis spp., Anoplocephalaspp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp.,Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp.,Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp.,Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilariaspp., Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobiusspp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsisspp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronemaspp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepisspp., Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylusspp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muelleriusspp., Necator spp., Nematodirus spp., Nippostrongylus spp.,Oesophagostomum spp., Ollulanus spp., Onchocerca spp., Opisthorchisspp., Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp.,Parafilaria spp., Paragonimus spp., Paramphistomum spp.,Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylusspp., Schistosoma spp., Setaria spp., Spirocerca spp., Stephanofilariaspp., Stephanurus spp., Strongyloides spp., Strongylus spp., Syngamusspp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp.,Toxocara spp., Trichinella spp., Trichobilharzia spp., Trichostrongylusspp., Trichuris spp., Uncinaria spp., Wuchereria spp.;

plant pests from the phylum of the Nematoda, i.e. phytoparasiticnematodes, especially Aglenchus spp., for example Aglenchus agricola,Anguina spp., for example Anguina tritici, Aphelenchoides spp., forexample Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimusspp., for example Belonolaimus gracilis, Belonolaimus longicaudatus,Belonolaimus nortoni, Bursaphelenchus spp., for example Bursaphelenchuscocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus,Cacopaurus spp., for example Cacopaurus pestis, Criconemella spp., forexample Criconemella curvata, Criconemella onoensis, Criconemellaornata, Criconemella rusium, Criconemella xenoplax (=Mesocriconemaxenoplax), Criconemoides spp., for example Criconemoides ferniae,Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., forexample Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., forexample Globodera pallida, Globodera rostochiensis, Helicotylenchusspp., for example Helicotylenchus dihystera, Hemicriconemoides spp.,Hemicycliophora spp., Heterodera spp., for example Heterodera avenae,Heterodera glycines, Heterodera schachtii, Hoplolaimus spp., Longidorusspp., for example Longidorus africanus, Meloidogyne spp., for exampleMeloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla,Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp.,Paraphelenchus spp., Paratrichodorus spp., for example Paratrichodorusminor, Pratylenchus spp., for example Pratylenchus penetrans,Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulciusspp., Radopholus spp., for example Radopholus citrophilus, Radopholussimilis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp.,Subanguina spp., Trichodorus spp., for example Trichodorus obtusus,Trichodorus primitivus, Tylenchorhynchus spp., for exampleTylenchorhynchus annulatus, Tylenchulus spp., for example Tylenchulussemipenetrans, Xiphinema spp., for example Xiphinema index.

In addition, it is possible to control, from the sub-kingdom of theProtozoa, the order of the Coccidia, for example Eimeria spp.

The compounds of the formula (I) can optionally, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, asmicrobicides or gametocides, for example as fungicides, antimycotics,bactericides, virucides (including agents against viroids) or as agentsagainst MLO (mycoplasma-like organisms) and RLO (rickettsia-likeorganisms). If appropriate, they can also be used as intermediates orprecursors for the synthesis of other active compounds.

Formulations

The present invention further relates to formulations and use formsprepared therefrom as pesticides, for example drench, drip and sprayliquors, comprising at least one compound of the formula (I). In somecases, the use forms comprise further pesticides and/or adjuvants whichimprove the action, such as penetrants, e.g. vegetable oils, for examplerapeseed oil, sunflower oil, mineral oils, for example paraffin oils,alkyl esters of vegetable fatty acids, for example rapeseed oil methylester or soya oil methyl ester, or alkanol alkoxylates and/or spreaders,for example alkylsiloxanes and/or salts, for example organic orinorganic ammonium or phosphonium salts, for example ammonium sulphateor diammonium hydrogenphosphate and/or retention promoters, for exampledioctyl sulphosuccinate or hydroxypropyl guar polymers and/orhumectants, for example glycerol and/or fertilizers, for exampleammonium-, potassium- or phosphorus-containing fertilizers.

Customary formulations are, for example, water-soluble liquids (SL),emulsion concentrates (EC), emulsions in water (EW), suspensionconcentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules(GR) and capsule concentrates (CS); these and further possibleformulation types are described, for example, by Crop Life Internationaland in Pesticide Specifications, Manual on development and use of FAOand WHO specifications for pesticides, FAO Plant Production andProtection Papers 173, prepared by the FAO/WHO Joint Meeting onPesticide Specifications, 2004, ISBN: 9251048576. The formulations, inaddition to one or more compounds of the formula (I), optionallycomprise further agrochemical active ingredients.

These are preferably formulations or use forms which compriseauxiliaries, for example extenders, solvents, spontaneity promoters,carriers, emulsifiers, dispersants, frost protectants, biocides,thickeners and/or further auxiliaries, for example adjuvants. Anadjuvant in this context is a component which enhances the biologicaleffect of the formulation, without the component itself having anybiological effect. Examples of adjuvants are agents which promoteretention, spreading, attachment to the leaf surface or penetration.

These formulations are prepared in a known way, for example by mixingthe compounds of the formula (I) with auxiliaries such as, for example,extenders, solvents and/or solid carriers and/or other auxiliaries suchas, for example, surfactants. The formulations are produced either insuitable facilities or else before or during application.

The auxiliaries used may be substances suitable for imparting specialproperties, such as certain physical, technical and/or biologicalproperties, to the formulation of the compounds of the formula (I), orto the use forms prepared from these formulations (for exampleready-to-use pesticides such as spray liquors or seed dressingproducts).

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, thesulphones and sulphoxides (such as dimethyl sulphoxide).

If the extender utilized is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Useful liquid solventsare essentially: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols such as butanol orglycol and their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulphoxide, and alsowater.

In principle, it is possible to use all suitable solvents. Examples ofsuitable solvents are aromatic hydrocarbons, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatic or chlorinated aliphatichydrocarbons, such as chlorobenzene, chloroethylene or methylenechloride, aliphatic hydrocarbons, such as cyclohexane, paraffins,petroleum fractions, mineral and vegetable oils, alcohols, such asmethanol, ethanol, isopropanol, butanol or glycol and their ethers andesters, ketones such as acetone, methyl ethyl ketone, methyl isobutylketone or cyclohexanone, strongly polar solvents, such as dimethylsulphoxide, and also water.

In principle, it is possible to use all suitable carriers. Usefulcarriers especially include: for example ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals such as finely divided silica, alumina and natural or syntheticsilicates, resins, waxes and/or solid fertilizers. Mixtures of suchcarriers can likewise be used. Useful carriers for granules include: forexample crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite, dolomite, and synthetic granules of inorganic andorganic meals, and also granules of organic material such as sawdust,paper, coconut shells, corn cobs and tobacco stalks.

Liquefied gaseous extenders or solvents can also be used. Especiallysuitable are those extenders or carriers which are gaseous at standardtemperature and under standard pressure, for example aerosol propellantssuch as halogenated hydrocarbons, and also butane, propane, nitrogen andcarbon dioxide.

Examples of emulsifiers and/or foam formers, dispersants or wettingagents with ionic or nonionic properties, or mixtures of thesesurfactants, include salts of polyacrylic acid, salts of lignosulphonicacid, salts of phenolsulphonic acid or naphthalenesulphonic acid,polycondensates of ethylene oxide with fatty alcohols or with fattyacids or with fatty amines, with substituted phenols (preferablyalkylphenols or arylphenols), salts of sulphosuccinic esters, taurinederivatives (preferably alkyl taurates), phosphoric esters ofpolyethoxylated alcohols or phenols, fatty acid esters of polyols, andderivatives of the compounds containing sulphates, sulphonates andphosphates, for example alkylaryl polyglycol ethers, alkylsulphonates,alkyl sulphates, arylsulphonates, protein hydrolysates, lignosulphitewaste liquors and methylcellulose. The presence of a surfactant isadvantageous if one of the compounds of the formula (I) and/or one ofthe inert carriers is insoluble in water and when the application takesplace in water.

Further auxiliaries which may be present in the formulations and the useforms derived therefrom include dyes such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organic dyessuch as alizarin dyes, azo dyes and metal phthalocyanine dyes, andnutrients and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

Additional components may be stabilizers, such as cold stabilizers,preservatives, antioxidants, light stabilizers, or other agents whichimprove the chemical and/or physical stability. Foam generators orantifoams may also be present.

In addition, the formulations and the use forms derived therefrom mayalso comprise, as additional auxiliaries, stickers such ascarboxymethylcellulose and natural and synthetic polymers in the form ofpowders, granules or latices, such as gum arabic, polyvinyl alcohol andpolyvinyl acetate, or else natural phospholipids such as cephalins andlecithins and synthetic phospholipids. Further possible auxiliaries aremineral and vegetable oils.

Optionally, further auxiliaries may be present in the formulations andthe use forms derived therefrom. Examples of such additives includefragrances, protective colloids, binders, adhesives, thickeners,thixotropic agents, penetrants, retention promoters, stabilizers,sequestrants, complexing agents, humectants, spreaders. In general, thecompounds of the formula (I) can be combined with any solid or liquidadditive commonly used for formulation purposes.

Useful retention promoters include all those substances which reduce thedynamic surface tension, for example dioctyl sulphosuccinate, orincrease the viscoelasticity, for example hydroxypropylguar polymers.

Suitable penetrants in the present context are all those substanceswhich are usually used for improving the penetration of agrochemicalactive compounds into plants. Penetrants are defined in this context bytheir ability to penetrate from the (generally aqueous) applicationliquor and/or from the spray coating into the cuticle of the plant andhence increase the mobility of the active compounds in the cuticle. Themethod described in the literature (Baur et al., 1997, Pesticide Science51, 131-152) can be used for determining this property. Examples includealcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecylethoxylate (12), fatty acid esters, for example rapeseed oil methylester or soya oil methyl ester, fatty amine alkoxylates, for exampletallowamine ethoxylate (15), or ammonium and/or phosphonium salts, forexample ammonium sulphate or diammonium hydrogenphosphate.

The formulations preferably comprise between 0.00000001% and 98% byweight of the compound of the formula (I) or, with particularpreference, between 0.01% and 95% by weight of the compound of theformula (I), more preferably between 0.5% and 90% by weight of thecompound of the formula (I), based on the weight of the formulation.

The content of the compound of the formula (I) in the use forms preparedfrom the formulations (in particular pesticides) may vary within wideranges. The concentration of the compound of the formula (I) in the useforms may typically be between 0.00000001% and 95% by weight of thecompound of the formula (I), preferably between 0.00001% and 1% byweight, based on the weight of the use form. The application isaccomplished in a customary manner appropriate for the use forms.

Mixtures

The compounds of the formula (I) may also be employed as a mixture withone or more suitable fungicides, bactericides, acaricides,molluscicides, nematicides, insecticides, microbiologicals, beneficialspecies, herbicides, fertilizers, bird repellents, phytotonics,sterilants, safeners, semiochemicals and/or plant growth regulators, inorder thus, for example, to broaden the spectrum of action, to prolongthe duration of action, to increase the rate of action, to preventrepulsion or prevent evolution of resistance. In addition, activecompound combinations of this kind can improve plant growth and/ortolerance to abiotic factors, for example high or low temperatures, todrought or to elevated water content or soil salinity. It is alsopossible to improve flowering and fruiting performance, optimizegermination capacity and root development, facilitate harvesting andimprove yields, influence maturation, improve the quality and/or thenutritional value of the harvested products, prolong storage life and/orimprove the processability of the harvested products.

Furthermore, the compounds of the formula (I) can be present in amixture with other active compounds or semiochemicals such asattractants and/or bird repellents and/or plant activators and/or growthregulators and/or fertilizers. Likewise, the compounds of the formula(I) can be used in mixtures with agents to improve plant properties, forexample growth, yield and quality of the harvested material.

In a particular embodiment of the invention, the compounds of theformula (I) are in the form of formulations or the use forms preparedfrom these formulations in a mixture with further compounds, preferablythose as described below.

If one of the compounds mentioned below can occur in various tautomericforms, these forms are also included even if not explicitly mentioned ineach case.

Insecticides/Acaricides/Nematicides

The active compounds identified here by their common names are known andare described, for example, in the pesticide handbook (“The PesticideManual” 16th Ed., British Crop Protection Council 2012) or can be foundon the Internet (e.g. http://www.alanwood.net/pesticides).

(1) Acetylcholinesterase (AChE) inhibitors, such as, for example,carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb,butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan,ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb,methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur,thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; ororganophosphates, for example acephate, azamethiphos, azinphos-ethyl,azinphos-methyl, cadusafos, chlorethoxy fos, chlorfenvinphos,chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos,demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate,dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur,fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos,isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate,isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos,monocrotophos, naled, omethoate, oxydemeton-methyl, parathion,parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon,phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos,pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos,temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfonand vamidothion.

(2) GABA-gated chloride channel antagonists, for examplecyclodiene-organochlorines, e.g. chlordane and endosulfan orphenylpyrazoles (fiproles), e.g. ethiprole and fipronil.

(3) Sodium channel modulators/voltage-gated sodium channel blockers, forexample pyrethroids, e.g. acrinathrin, allethrin, d-cis-trans allethrin,d-trans allethrin, bifenthrin, bioallethrin, bioallethrinS-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin,beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin,cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin,zeta-cypermethrin, cyphenothrin [(1R)-trans isomers], deltamethrin,empenthrin [(EZ)-(1R) isomers], esfenvalerate, etofenprox,fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate,halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R)-transisomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen,tefluthrin, tetramethrin, tetramethrin [(1R) isomers], tralomethrin andtransfluthrin or DDT or methoxychlor.

(4) Nicotinergic acetylcholine receptor (nAChR) agonists, for exampleneonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine orsulfoxaflor.

(5) Allosteric activators of the nicotinergic acetylcholine receptor(nAChR), for example spinosyns, e.g. spinetoram and spinosad.

(6) Chloride channel activators, for example avermectins/milbemycins,e.g. abamectin, emamectin benzoate, lepimectin and milbemectin.

(7) Juvenile hormone imitators, for example, juvenile hormone analogues,e.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

(8) Active compounds with unknown or nonspecific mechanisms of action,for example alkyl halides, e.g. methyl bromide and other alkyl halides;or chloropicrine or sulphuryl fluoride or borax or tartar emetic.

(9) Selective antifeedants, e.g. pymetrozine or flonicamid.

(10) Mite growth inhibitors, e.g. clofentezine, hexythiazox anddiflovidazin or etoxazole.

(11) Microbial disruptors of the insect gut membrane, e.g. Bacillusthuringiensis subspecies israelensis, Bacillus sphaericus, Bacillusthuringiensis subspecies aizawai, Bacillus thuringiensis subspecieskurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plantproteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb,Cry34/35Ab 1.

(12) Oxidative phosphorylation inhibitors, ATP disruptors, for examplediafenthiuron or organotin compounds, e.g. azocyclotin, cyhexatin andfenbutatin oxide or propargite or tetradifon.

(13) Oxidative phosphorylation decouplers that interrupt the H protongradient, for example chlorfenapyr, DNOC and sulfluramid.

(14) Nicotinergic acetylcholine receptor antagonists, for examplebensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.

(15) Chitin biosynthesis inhibitors, type 0, for example bistrifluron,chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron,hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron andtriflumuron.

(16) Chitin biosynthesis inhibitors, type 1, for example buprofezin.

(17) Moulting inhibitors (in particular for Diptera, i.e. dipterans)such as, for example, cyromazine.

(18) Ecdysone receptor agonists, for example chromafenozide,halofenozide, methoxyfenozide and tebufenozide.

(19) Octopaminergic agonists, for example amitraz.

(20) Complex-III electron transport inhibitors, for examplehydramethylnon or acequinocyl or fluacrypyrim.

(21) Complex-I electron transport inhibitors, for example METIacaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben,tebufenpyrad and tolfenpyrad or rotenone (Derris).

(22) Voltage-gated sodium channel blockers, for example indoxacarb ormetaflumizone.

(23) Inhibitors of acetyl-CoA carboxylase, for example tetronic andtetramic acid derivatives, e.g. spirodiclofen, spiromesifen andspirotetramat.

(24) Complex-IV electron transport inhibitors, for example phosphines,e.g. aluminium phosphide, calcium phosphide, phosphine and zincphosphide or cyanide.

(25) Complex-II electron transport inhibitors, for example cyenopyrafenand cyflumetofen.

(28) Ryanodine receptor effectors, for example diamides, e.g.chlorantraniliprole, cyantraniliprole and flubendiamide,

further active compounds, for example afidopyropen, azadirachtin,benclothiaz, benzoximate, bifenazate, bromopropylate, chinomethionat,cryolite,

dicofol, diflovidazin, fluensulfone, flometoquin, flufenerim,flufenoxystrobin, flufiprole, fluopyram, flupyradifurone, fufenozide,heptafluthrin, imidaclothiz, iprodione, meperfluthrin, paichongding,pyflubumide, pyrifluquinazon, pyriminostrobin, tetramethylfluthrin andiodomethane; and also preparations based on Bacillus firmus (I-1582,BioNeem, Votivo), and also the following compounds:3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide(known from WO2005/077934) and1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO2006/043635),{1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4′-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone(known from WO2003/106457),2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide(known from WO2006/003494),3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one(known from WO2009/049851),3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonate(known from WO2009/049851),4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine(known from WO2004/099160),4-(but-2-yn-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known fromWO2003/076415), PF1364 (CAS Reg. No. 1204776-60-2),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}benzamide(known from WO2005/085216),4-{5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl}-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}-1-naphthamide(known from WO2009/002809), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylate(known from WO2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazinecarboxylate(known from WO2005/085216), methyl2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate(known from WO2005/085216), methyl2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazinecarboxylate(known from WO2005/085216),1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide(known from WO2010/069502),N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide(known from CN102057925),3-chloro-N-(2-cyanopropan-2-yl)-N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl]phthalamide(known from WO2012/034472),8-chloro-N-[(2-chloro-5-methoxyphenyl)sulphonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide(known from WO2010/129500),4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxidothietan-3-yl)benzamide(known from WO2009/080250),N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(known from WO2012/029672),1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate(known from WO2009/099929),1-[(6-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate(known from WO2009/099929),(5S,8R)-1-[(6-chloropyridin-3-yl)methyl]-9-nitro-2,3,5,6,7,8-hexahydro-1H-5,8-epoxyimidazo[1,2-a]azepine(known from WO2010/069266),(2E)-1-[(6-chloropyridin-3-yl)methyl]-N′-nitro-2-pentylidenehydrazinecarboximidamide(known from WO2010/060231),4-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en-1-yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluoromethyl)pyrimidine(known from CN101337940),N-[2-(tert-butylcarbamoyl)-4-chloro-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide(known from WO2008/134969).

Fungicides

The active compounds specified herein by their common name are known anddescribed, for example, in “Pesticide Manual” or on the Internet (forexample: http://www.alanwood.net/pesticides).

(1) Ergosterol biosynthesis inhibitors, for example (1.1) aldimorph,(1.2) azaconazole, (1.3) bitertanol, (1.4) bromuconazole, (1.5)cyproconazole, (1.6) diclobutrazole, (1.7) difenoconazole, (1.8)diniconazole, (1.9) diniconazole-M, (1.10) dodemorph, (1.11) dodemorphacetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol,(1.15) fenbuconazole, (1.16) fenhexamid, (1.17) fenpropidin, (1.18)fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21)flusilazole, (1.22) flutriafole, (1.23) furconazole, (1.24)furconazole-cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) imazalilsulphate, (1.28) imibenconazole, (1.29) ipconazole, (1.30) metconazole,(1.31) myclobutanil, (1.32) naftifin, (1.33) nuarimol, (1.34)oxpoconazole, (1.35) paclobutrazole, (1.36) pefurazoate, (1.37)penconazole, (1.38) piperalin, (1.39) prochloraz, (1.40) propiconazole,(1.41) prothioconazole, (1.42) pyributicarb, (1.43) pyrifenox, (1.44)quinconazole, (1.45) simeconazole, (1.46) spiroxamine, (1.47)tebuconazole, (1.48) terbinafin, (1.49) tetraconazole, (1.50)triadimefon, (1.51) triadimenol, (1.52) tridemorph, (1.53) triflumizole,(1.54) triforine, (1.55) triticonazole, (1.56) uniconazole, (1.57)uniconazole-P, (1.58) viniconazole, (1.59) voriconazole, (1.60)1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, (1.61) methyl1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,(1.62)N′-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide,(1.63)N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamideand (1.64)O-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]-1H-imidazole-1-carbothioate,(1.65) pyrisoxazole.

(2) Respiration inhibitors (respiratory chain inhibitors), for example(2.1) bixafen, (2.2) boscalid, (2.3) carboxin, (2.4) diflumetorim, (2.5)fenfuram, (2.6) fluopyram, (2.7) flutolanil, (2.8) fluxapyroxad, (2.9)furametpyr, (2.10) furmecyclox, (2.11) isopyrazam mixture of thesyn-epimeric racemate 1RS,4SR,9RS and the anti-empimeric racemate1RS,4SR,9SR, (2.12) isopyrazam (anti-epimeric racemate), (2.13)isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.14) isopyrazam(anti-epimeric enantiomer 1S,4R,9R), (2.15) isopyrazam (syn-epimericracemate 1RS,4SR,9RS), (2.16) isopyrazam (syn-epimeric enantiomer1R,4S,9R), (2.17) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.18)mepronil, (2.19) oxycarboxin, (2.20) penflufen, (2.21) penthiopyrad,(2.22) sedaxane, (2.23) thifluzamide, (2.24)1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,(2.25)3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide,(2.26)3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide,(2.27)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.28)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazoline-4-amine,(2.29) benzovindiflupyr, (2.30)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamideand (2.31)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.32)3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.33)1,3,5-trimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.34)1-methyl-3-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.35)1-methyl-3-(trifluoromethyl)-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.36)1-methyl-3-(trifluoromethyl)-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.37)3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.38)3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.39)1,3,5-trimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.40)1,3,5-trimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.41) benodanil, (2.42)2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,(2.43) isofetamid.

(3) Respiration inhibitors (respiratory chain inhibitors) that act oncomplex III of the respiratory chain, for example (3.1) ametoctradin,(3.2) amisulbrom, (3.3) azoxystrobin, (3.4) cyazofamid, (3.5)coumethoxystrobin, (3.6) coumoxystrobin, (3.7) dimoxystrobin, (3.8)enestroburin, (3.9) famoxadone, (3.10) fenamidone, (3.11)flufenoxystrobin, (3.12) fluoxastrobin, (3.13) kresoxim-methyl, (3.14)metominostrobin, (3.15) orysastrobin, (3.16) picoxystrobin, (3.17)pyraclostrobin, (3.18) pyrametostrobin, (3.19) pyraoxystrobin, (3.20)pyribencarb, (3.21) triclopyricarb, (3.22) trifloxystrobin, (3.23)(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide,(3.24)(2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide,(3.25)(2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide,(3.26)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,(3.27)(2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,(3.28)2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,(3.29)5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one,(3.30) methyl(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulphanypmethyl]phenyl}-3-methoxyprop-2-enoate,(3.31)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide,(3.32)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide(4) inhibitors of mitosis and cell division, for example (4.1) benomyl,(4.2) carbendazim, (4.3) chlorfenazole, (4.4) diethofencarb, (4.5)ethaboxam, (4.6) fluopicolid, (4.7) fuberidazole, (4.8) pencycuron,(4.9) thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate,(4.12) zoxamide, (4.13)5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidineand (4.14)3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyppyridazine.

(5) Compounds having multisite activity such as, for example, (5.1)Bordeaux mixture, (5.2) captafol, (5.3) captan, (5.4) chlorothalonil,(5.5) copper preparations such as copper hydroxide, (5.6) coppernaphthenate, (5.7) copper oxide, (5.8) copper oxychloride, (5.9) coppersulphate, (5.10) dichlofluanid, (5.11) dithianon, (5.12) dodine, (5.13)dodine free base, (5.14) ferbam, (5.15) fluorfolpet, (5.16) folpet,(5.17) guazatine, (5.18) guazatine acetate, (5.19) iminoctadine, (5.20)iminoctadine albesilate, (5.21) iminoctadine triacetate, (5.22)mancopper, (5.23) mancozeb, (5.24) maneb, (5.25) metiram, (5.26) zincmetiram, (5.27) copper-oxine, (5.28) propamidine, (5.29) propineb,(5.30) sulphur and sulphur preparations such as, for example, calciumpolysulphide, (5.31) thiram, (5.32) tolylfluanid, (5.33) zineb, (5.34)ziram and (5.35) anilazine.

(6) Resistance inducers, for example (6.1) acibenzolar-S-methyl, (6.2)isotianil, (6.3) probenazole, (6.4) tiadinil and (6.5) laminarin

(7) Amino acid and protein biosynthesis inhibitors, for example (7.1),(7.2) blasticidin-S, (7.3) cyprodinil, (7.4) kasugamycin, (7.5)kasugamycin hydrochloride hydrate, (7.6) mepanipyrim, (7.7)pyrimethanil, (7.8)3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinolineand (7.9) oxytetracycline and (7.10) streptomycin.

(8) ATP production inhibitors such as, for example, (8.1) fentinacetate, (8.2) fentin chloride, (8.3) fentin hydroxide and (8.4)silthiofam.

(9) Cell wall synthesis inhibitors, for example (9.1) benthiavalicarb,(9.2) dimethomorph, (9.3) flumorph, (9.4) iprovalicarb, (9.5)mandipropamid, (9.6) polyoxins, (9.7) polyoxorim, (9.8) validamycin A,(9.9) valifenalate and (9.10) polyoxin B.

(10) Lipid and membrane synthesis inhibitors, for example (10.1)biphenyl, (10.2) chlorneb, (10.3) dicloran, (10.4) edifenphos, (10.5)etridiazole, (10.6) iodocarb, (10.7) iprobenfos, (10.8) isoprothiolane,(10.9) propamocarb, (10.10) propamocarb hydrochloride, (10.11)prothiocarb, (10.12) pyrazophos, (10.13) quintozene, (10.14) tecnazeneand (10.15) tolclofos-methyl.

(11) Melanin biosynthesis inhibitors, for example (11.1) carpropamid,(11.2) diclocymet, (11.3) fenoxanil, (11.4) fthalide, (11.5) pyroquilon,(11.6) tricyclazole and (11.7) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

(12) Nucleic acid synthesis inhibitors, for example (12.1) benalaxyl,(12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate, (12.4) clozylacon,(12.5) dimethirimol, (12.6) ethirimol, (12.7) furalaxyl, (12.8)hymexazole, (12.9) metalaxyl, (12.10) metalaxyl-M (mefenoxam), (12.11)ofurace, (12.12) oxadixyl, (12.13) oxolinic acid and (12.14)octhilinone.

(13) Signal transduction inhibitors, for example (13.1) chlozolinate,(13.2) fenpiclonil, (13.3) fludioxonil, (13.4) iprodione, (13.5)procymidone, (13.6) quinoxyfen, (13.7) vinclozolin and (13.8)proquinazid.

(14) Decouplers, for example (14.1) binapacryl, (14.2) dinocap, (14.3)ferimzone, (14.4) fluazinam and (14.5) meptyldinocap.

(15) Further compounds, for example (15.1) benthiazole, (15.2)bethoxazine, (15.3) capsimycin, (15.4) carvone, (15.5) quinomethionate,(15.6) pyriofenone (chlazafenone), (15.7) cufraneb, (15.8) cyflufenamid,(15.9) cymoxanil, (15.10) cyprosulfamide, (15.11) dazomet, (15.12)debacarb, (15.13) dichlorophen, (15.14) diclomezine, (15.15)difenzoquat, (15.16) difenzoquat methylsulphate, (15.17) diphenylamine,(15.18) EcoMate, (15.19) fenpyrazamine, (15.20) flumetover, (15.21)fluorimid, (15.22) flusulfamide, (15.23) flutianil, (15.24)fosetyl-aluminium, (15.25) fosetyl-calcium, (15.26) fosetyl-sodium,(15.27) hexachlorobenzene, (15.28) irumamycin, (15.29) methasulfocarb,(15.30) methyl isothiocyanate, (15.31) metrafenone, (15.32) mildiomycin,(15.33) natamycin, (15.34) nickel dimethyldithiocarbamate, (15.35)nitrothal-isopropyl, (15.36) octhilinone, (15.37) oxamocarb, (15.38)oxyfenthiin, (15.39) pentachlorophenol and its salts, (15.40)phenothrin, (15.41) phosphoric acid and its salts, (15.42)propamocarb-fosetylate, (15.43) propanosine-sodium, (15.44) pyrimorph,(15.45)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(15.46)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(15.47) pyrrolnitrin, (15.48) tebufloquin, (15.49) tecloftalam, (15.50)tolnifanide, (15.51) triazoxide, (15.52) trichlamide, (15.53) zarilamid,(15.54)(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate, (15.55)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.56)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.57)1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.58) 1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl1H-imidazole-1-carboxylate, (15.59)2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine, (15.60)2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, (15.61)2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone,(15.62)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,(15.63)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone,(15.64)2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone,(15.65) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.66)2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine,(15.67) 2-phenylphenol and salts, (15.68)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.69) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (15.70)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(15.71)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(15.72) 5-amino-1,3,4-thiadiazole-2-thiol, (15.73)5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene-2-sulphonohydrazide,(15.74) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4-amine, (15.75)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidine-4-amine, (15.76)5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidine-7-amine, (15.77) ethyl(2Z)-3-amino-2-cyano-3-phenylacrylate, (15.78)N′-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(15.79)N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,(15.80)N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,(15.81)N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide,(15.82)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,(15.83)N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide,(15.84)N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,(15.85)N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,(15.86)N′-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methylimidoformamide,(15.87)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide,(15.88)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,(15.89)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,(15.90) pentyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.91) phenazine-1-carboxylic acid, (15.92) quinolin-8-ol, (15.93)quinolin-8-ol sulphate (2:1), (15.94) tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.95)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.96)N-(4′-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.97)N-(2′,4′-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.98)3-(difluoromethyl)-1-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.99)N-(2′,5′-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,(15.100)3-(difluoromethyl)-1-methyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.101)5-fluoro-1,3-dimethyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(15.102) 2-chloro-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.103)3-(difluoromethyl)-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,(15.104)N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.105)3-(difluoromethyl)-N-(4′-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide,(15.106)N-(4′-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.107) 2-chloro-N-(4′-ethynylbiphenyl-2-yl)nicotinamide, (15.108)2-chloro-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.109)4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide,(15.110)5-fluoro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.111)2-chloro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.112)3-(difluoromethyl)-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,(15.113)5-fluoro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide,(15.114)2-chloro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide,(15.115)(5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone,(15.116)N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulphonyl)valinamide,(15.117) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.118)but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenypmethylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.119) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form:4-amino-5-fluoropyrimidin-2(1H)-one), (15.120) propyl3,4,5-trihydroxybenzoate, (15.121)1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(15.122)1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(15.123)1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(15.124)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.125)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.126)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(15.127)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenypoxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.128)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (15.129)5-(allylsulphanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenypoxiran-2-yl]methyl}-1H-1,2,4-triazole,(15.130)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.131)2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.132)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.133)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (15.134)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (15.135)5-(allylsulphanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenypoxiran-2-yl]methyl}-1H-1,2,4-triazole,(15.136)5-(allylsulphanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(15.137)2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.138)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.139)2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.140)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.141)2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.142)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.143)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.144)2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(15.145)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide,(15.146) 2-(6-benzylpyridin-2-yl)quinazoline, (15.147)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,(15.148)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.149) abscisic acid, (15.150)3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide,(15.151)N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide,(15.152)N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.153)N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.154)N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.155)N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.156)N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(15.157)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.158)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.159)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.160)N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.161)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.162)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.163)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.164)N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.165)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.166)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.167)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.168)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(15.169)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.170)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.171)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.172)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide,(15.173)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.174)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.175)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(15.176)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carbothioamide,(15.177)3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide,(15.178)3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(15.179)3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(15.180)N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,(15.181)N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide,(15.182)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine.All the mixing components mentioned in classes (1) to (15), as the casemay be, may form salts with suitable bases or acids if they are capableof doing so on the basis of their functional groups.

Biological Pesticides as Mixing Components

The compounds of the formula (I) can be combined with biologicalpesticides.

Biological pesticides include especially bacteria, fungi, yeasts, plantextracts and products formed by microorganisms, including proteins andsecondary metabolites.

Biological pesticides include bacteria such as spore-forming bacteria,root-colonizing bacteria and bacteria which act as biologicalinsecticides, fungicides or nematicides.

Examples of such bacteria which are used or can be used as biologicalpesticides are:

Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacilluscereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus,strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, inparticular strain GB34 (Accession No. ATCC 700814) and strain QST2808(Accession No. NRRL B-30087), or Bacillus subtilis, in particular strainGB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713(Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002(Accession No. NRRL B-50421), or Bacillus thuringiensis, in particularB. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52(Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, inparticular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp.kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulusreniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomycesmicroflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), Streptomycesgalbus strain AQ 6047 (Accession Number NRRL 30232).

Examples of fungi and yeasts which are used or can be used as biologicalpesticides are:

Beauveria bassiana, in particular strain ATCC 74040, Coniothyriumminitans, in particular strain CON/M/91-8 (Accession No. DSM-9660),Lecanicillium spp., in particular strain HRO LEC 12, Lecanicilliumlecanii, (formerly known as Verticillium lecanii), in particular strainKV01, Metarhizium anisopliae, in particular strain F52 (DSM3884/ATCC90448), Metschnikowia fructicola, in particular strain NRRL Y-30752,Paecilomyces fumosoroseus (now: Isaria fumosorosea), in particularstrain IFPC 200613, or strain Apopka 97 (Accession No. ATCC 20874),Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL89/030550), Talaromyces flavus, in particular strain V117b, Trichodermaatroviride, in particular strain SC1 (Accession Number CBS 122089),Trichoderma harzianum, in particular T. harzianum rifai T39 (AccessionNumber CNCM 1-952).

Examples of viruses which are used or can be used as biologicalpesticides are:

Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydiapomonella (codling moth) granulosis virus (GV), Helicoverpa armigera(cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua(beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV,Spodoptera littoralis (African cotton leafworm) NPV.

Also included are bacteria and fungi which are added as ‘inoculant’ toplants or plant parts or plant organs and which, by virtue of theirparticular properties, promote plant growth and plant health. Examplesinclude:

Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp.,Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., especiallyBurkholderia cepacia (formerly known as Pseudomonas cepacia), Gigasporaspp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillusbuchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp.,Rhizobium spp., especially Rhizobium trifolii, Rhizopogon spp.,Scleroderma spp., Suillus spp., Streptomyces spp.

Examples of plant extracts and products formed by microorganisms,including proteins and secondary metabolites, which are used or can beused as biological pesticides are:

Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassianigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin,Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza,Fungastop, Heads Up (Chenopodium quinoa saponin extract),pyrethrum/pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,“Requiem™ Insecticide”, rotenone, ryania/ryanodine, Symphytumofficinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulummajus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract,especially oilseed rape powder or mustard powder.

Safeners as Mixing Components

The compounds of the formula (I) can be combined with safeners, forexample benoxacor, cloquintocet(-mexyl), cyometrinil, cyprosulfamide,dichlormid, fenchlorazole(-ethyl), fenclorim, flurazole, fluxofenim,furilazole, isoxadifen(-ethyl), mefenpyr(-diethyl), naphthalicanhydride, oxabetrinil,2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulphonyl)benzamide (CAS129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4).

Plants and Plant Parts

All plants and plant parts can be treated in accordance with theinvention. Plants are understood here to mean all plants and populationsof plants, such as desirable and undesirable wild plants or crop plants(including naturally occurring crop plants), for example cereals (wheat,rice, triticale, barley, rye, oats), maize, soya bean, potato, sugarbeet, sugar cane, tomatoes, peas and other vegetable species, cotton,tobacco, oilseed rape, and also fruit plants (with the fruits apples,pears, citrus fruits and grapes). Crop plants may be plants which can beobtained by conventional breeding and optimization methods or bybiotechnological and genetic engineering methods or combinations ofthese methods, including the transgenic plants and including the plantcultivars which are protectable and non-protectable by plant breeders'rights. Plant parts shall be understood to mean all parts and organs ofthe plants above and below ground, such as shoot, leaf, flower and root,examples given being leaves, needles, stalks, stems, flowers, fruitbodies, fruits and seeds, and also roots, tubers and rhizomes. Plantparts also include harvested material and vegetative and generativepropagation material, for example cuttings, tubers, rhizomes, slips andseeds.

The inventive treatment of the plants and parts of plants with thecompounds of the formula (I) is effected directly or by allowing them toact on the surroundings, habitat or storage space thereof by thecustomary treatment methods, for example by dipping, spraying,evaporating, fogging, scattering, painting on, injecting, and, in thecase of propagation material, especially in the case of seeds, also byapplying one or more coats.

As already mentioned above, it is possible to treat all plants and partsthereof in accordance with the invention. In a preferred embodiment,wild plant species and plant cultivars, or those obtained byconventional biological breeding methods, such as crossing or protoplastfusion, and parts thereof, are treated. In a further preferredembodiment, transgenic plants and plant cultivars obtained by geneticengineering methods, if appropriate in combination with conventionalmethods (genetically modified organisms), and parts thereof are treated.The term “parts” or “parts of plants” or “plant parts” has beenexplained above. Particular preference is given in accordance with theinvention to treating plants of the respective commercially customaryplant cultivars or those that are in use. Plant cultivars are understoodto mean plants having new properties (“traits”) and which have beengrown by conventional breeding, by mutagenesis or by recombinant DNAtechniques. They may be cultivars, varieties, biotypes or genotypes.

Transgenic plants, seed treatment and integration events

The preferred transgenic plants or plant cultivars (those obtained bygenetic engineering) which are to be treated in accordance with theinvention include all plants which, through the genetic modification,received genetic material which imparts particular advantageous usefulproperties (“traits”) to these plants. Examples of such properties arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to levels of water or soil salinity,enhanced flowering performance, easier harvesting, accelerated ripening,higher harvest yields, higher quality and/or higher nutritional value ofthe harvested products, better storage life and/or processability of theharvested products. Further and particularly emphasized examples of suchproperties are increased resistance of the plants against animal andmicrobial pests, such as insects, arachnids, nematodes, mites, slugs andsnails, owing, for example, to toxins formed in the plants, inparticular those formed in the plants by the genetic material fromBacillus thuringiensis (for example by the genes CryIA(a), CryIA(b),CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF andalso combinations thereof), and also increased resistance of the plantsagainst phytopathogenic fungi, bacteria and/or viruses caused, forexample, by systemic acquired resistance (SAR), systemin, phytoalexins,elicitors and resistance genes and correspondingly expressed proteinsand toxins, and also increased tolerance of the plants to certain activeherbicidal ingredients, for example imidazolinones, sulphonylureas,glyphosates or phosphinothricin (for example the “PAT” gene). The geneswhich impart the desired properties (“traits”) in question may also bepresent in combinations with one another in the transgenic plants.Examples of transgenic plants include the important crop plants, such ascereals (wheat, rice, triticale, barley, rye, oats), maize, soya beans,potatoes, sugar beet, sugar cane, tomatoes, peas and other types ofvegetable, cotton, tobacco, oilseed rape and also fruit plants (with thefruits apples, pears, citrus fruits and grapevines), particular emphasisbeing given to maize, soya beans, wheat, rice, potatoes, cotton, sugarcane, tobacco and oilseed rape. Properties (“traits”) which areparticularly emphasized are the increased resistance of the plants toinsects, arachnids, nematodes and slugs and snails.

Crop Protection—Types of Treatment

The treatment of the plants and plant parts with the compounds of theformula (I) is carried out directly or by action on their surroundings,habitat or storage space using customary treatment methods, for exampleby dipping, spraying, atomizing, irrigating, evaporating, dusting,fogging, broadcasting, foaming, painting, spreading-on, injecting,watering (drenching), drip irrigating and, in the case of propagationmaterial, in particular in the case of seed, furthermore as a powder fordry seed treatment, a solution for liquid seed treatment, awater-soluble powder for slurry treatment, by incrusting, by coatingwith one or more coats, etc. It is furthermore possible to apply thecompounds of the formula (I) by the ultra-low volume method or to injectthe application form or the compound of the formula (I) itself into thesoil.

A preferred direct treatment of the plants is foliar application, i.e.the compounds of the formula (I) are applied to the foliage, wheretreatment frequency and the application rate should be adjustedaccording to the level of infestation with the pest in question.

In the case of systemically active compounds, the compounds of theformula (I) also access the plants via the root system. The plants arethen treated by the action of the compounds of the formula (I) on thehabitat of the plant. This can be accomplished, for example, bydrenching, or by mixing into the soil or the nutrient solution, meaningthat the locus of the plant (e.g. soil or hydroponic systems) isimpregnated with a liquid form of the compounds of the formula (I), orby soil application, meaning that the compounds of the formula (I) areintroduced in solid form (e.g. in the form of granules) into the locusof the plants. In the case of paddy rice crops, this can also beaccomplished by metering the compound of the formula (I) in a solidapplication form (for example as granules) into a flooded paddy field.

Seed Treatment

The control of animal pests by the treatment of the seed of plants haslong been known and is the subject of constant improvement. However, thetreatment of seed entails a series of problems which cannot always besolved in a satisfactory manner Thus, it is desirable to develop methodsfor protecting the seed and the germinating plant which dispense with,or at least reduce considerably, the additional application ofpesticides during storage, after sowing or after emergence of theplants. It is additionally desirable to optimize the amount of activecompound used so as to provide optimum protection for the seed and thegerminating plant from attack by animal pests, but without damage to theplant itself by the active compound used. In particular, methods for thetreatment of seed should also take account of the intrinsic insecticidalor nematicidal properties of pest-resistant or -tolerant transgenicplants in order to achieve optimal protection of the seed and thegerminating plant with a minimum expenditure of pesticides.

The present invention therefore in particular also relates to a methodfor the protection of seed and germinating plants, from attack by pests,by treating the seed with one of the compounds of the formula (I). Themethod according to the invention for protecting seed and germinatingplants against attack by pests further comprises a method in which theseed is treated simultaneously in one operation or sequentially with acompound of the formula (I) and a mixing component. It also furthercomprises a method where the seed is treated at different times with acompound of the formula (I) and a mixing component.

The invention likewise relates to the use of the compounds of theformula (I) for the treatment of seed for protecting the seed and theresulting plant from animal pests.

The invention further relates to seed which has been treated with acompound of the formula (I) for protection from animal pests. Theinvention also relates to seed which has been treated simultaneouslywith a compound of the formula (I) and a mixing component. The inventionfurther relates to seed which has been treated at different times with acompound of the formula (I) and a mixing component. In the case of seedwhich has been treated at different times with a compound of the formula(I) and a mixing component, the individual substances may be present onthe seed in different layers. In this case, the layers comprising acompound of the formula (I) and mixing components may optionally beseparated by an intermediate layer. The invention also relates to seedin which a compound of the formula (I) and a mixing component have beenapplied as part of a coating or as a further layer or further layers inaddition to a coating.

The invention further relates to seed which, after the treatment with acompound of the formula (I), is subjected to a film-coating process toprevent dust abrasion on the seed.

One of the advantages encountered with a systemically acting compound ofthe formula (I) is the fact that, by treating the seed, not only theseed itself but also the plants resulting therefrom are, afteremergence, protected against animal pests. In this way, the immediatetreatment of the crop at the time of sowing or shortly thereafter can bedispensed with.

A further advantage is that the treatment of the seed with a compound ofthe formula (I) can enhance germination and emergence of the treatedseed.

It is likewise considered to be advantageous that compounds of theformula (I) can especially also be used for transgenic seed.

Furthermore, compounds of the formula (I) can be employed in combinationwith compositions of signalling technology, leading to bettercolonization by symbionts such as, for example, rhizobia, mycorrhizaeand/or endophytic bacteria or fungi, and/or to optimized nitrogenfixation.

The compounds of the formula (I) are suitable for protection of seed ofany plant variety which is used in agriculture, in the greenhouse, inforests or in horticulture. More particularly, this includes seed ofcereals (for example wheat, barley, rye, millet and oats), maize,cotton, soya beans, rice, potatoes, sunflowers, coffee, tobacco, canola,oilseed rape, beet (for example sugar beet and fodder beet), peanuts,vegetables (for example tomatoes, cucumbers, beans, cruciferousvegetables, onions and lettuce), fruit plants, lawns and ornamentalplants. Of particular significance is the treatment of the seed ofcereals (such as wheat, barley, rye and oats), maize, soya bean, cotton,canola, oilseed rape and rice.

As already mentioned above, the treatment of transgenic seed with acompound of the formula (I) is also of particular importance. Thisinvolves the seed of plants which generally contain at least oneheterologous gene which controls the expression of a polypeptide havinginsecticidal and/or nematicidal properties in particular. Theheterologous genes in transgenic seed may originate from microorganismssuch as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma,Clavibacter, Glomus or Gliocladium. The present invention isparticularly suitable for the treatment of transgenic seed containing atleast one heterologous gene originating from Bacillus sp. Theheterologous gene is more preferably derived from Bacillusthuringiensis.

In the context of the present invention, the compound of the formula (I)is applied to the seed. The seed is preferably treated in a state inwhich it is sufficiently stable for no damage to occur in the course oftreatment. In general, the seed can be treated at any time betweenharvest and sowing. It is customary to use seed which has been separatedfrom the plant and freed from cobs, shells, stalks, coats, hairs or theflesh of the fruits. For example, it is possible to use seed which hasbeen harvested, cleaned and dried down to a moisture content whichallows storage. Alternatively, it is also possible to use seed which,after drying, has been treated with, for example, water and then driedagain, for example priming. In the case of rice seed, it is alsopossible to use seed which has been imbibed in water up to a certainstage (pigeon breast stage) for example, which leads to improvedgermination and more uniform emergence.

When treating the seed, care must generally be taken that the amount ofthe compound of the formula (I) applied to the seed and/or the amount offurther additives is chosen in such a way that the germination of theseed is not adversely affected, or that the resulting plant is notdamaged. This has to be ensured particularly in the case of activecompounds which can exhibit phytotoxic effects at certain applicationrates.

In general, the compounds of the formula (I) are applied to the seed inthe form of a suitable formulation. Suitable formulations and processesfor seed treatment are known to the person skilled in the art.

The compounds of the formula (I) can be converted to the customaryseed-dressing formulations, such as solutions, emulsions, suspensions,powders, foams, slurries or other coating compositions for seed, andalso ULV formulations.

These formulations are prepared in a known manner, by mixing thecompounds of the formula (I) with customary additives such as, forexample, customary extenders and also solvents or diluents, colorants,wetting agents, dispersants, emulsifiers, antifoams, preservatives,secondary thickeners, adhesives, gibberellins and also water.

Colorants which may be present in the seed-dressing formulations usablein accordance with the invention are all colorants which are customaryfor such purposes. It is possible to use either pigments, which aresparingly soluble in water, or dyes, which are soluble in water.Examples include the dyes known by the names Rhodamine B, C.I. PigmentRed 112 and C.I. Solvent Red 1.

Useful wetting agents which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are customary for the formulation ofactive agrochemical compounds. Preference is given to using alkylnaphthalenesulphonates, such as diisopropyl or diisobutylnaphthalenesulphonates.

Suitable dispersants and/or emulsifiers which may be present in theseed-dressing formulations usable in accordance with the invention areall nonionic, anionic and cationic dispersants customary for theformulation of active agrochemical compounds. Preference is given tousing nonionic or anionic dispersants or mixtures of nonionic or anionicdispersants. Suitable nonionic dispersants include in particularethylene oxide/propylene oxide block polymers, alkylphenol polyglycolethers and tristyrylphenol polyglycol ethers, and the phosphated orsulphated derivatives thereof. Suitable anionic dispersants areespecially lignosulphonates, polyacrylic acid salts andarylsulphonate/formaldehyde condensates.

Antifoams which may be present in the seed-dressing formulations usablein accordance with the invention are all foam-inhibiting substancescustomary for formulation of active agrochemical compounds. Siliconeantifoams and magnesium stearate can be used with preference.

Preservatives which may be present in the seed-dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich can be used for such purposes in agrochemical compositions.Preferred examples include cellulose derivatives, acrylic acidderivatives, xanthan, modified clays and finely divided silica.

Useful stickers which may be present in the seed-dressing formulationsusable in accordance with the invention are all customary binders usablein seed-dressing products. Preferred examples includepolyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

Gibberellins which may be present in the seed-dressing formulationsusable in accordance with the invention are preferably the gibberellinsA1, A3 (=gibberellic acid), A4 and A7; particular preference is given tousing gibberellic acid. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutzund Schädlingsbekämpfungsmittel”, vol. 2,Springer Verlag, 1970, pp. 401-412).

The seed-dressing formulations usable in accordance with the inventioncan be used to treat a wide variety of different kinds of seed, eitherdirectly or after prior dilution with water. For instance, theconcentrates or the preparations obtainable therefrom by dilution withwater can be used to dress the seed of cereals, such as wheat, barley,rye, oats, and triticale, and also the seed of maize, rice, oilseedrape, peas, beans, cotton, sunflowers, soya beans and beets, or else awide variety of different vegetable seed. The seed-dressing formulationsusable in accordance with the invention, or the dilute use formsthereof, can also be used to dress seed of transgenic plants.

For treatment of seed with the seed-dressing formulations usable inaccordance with the invention, or the use forms prepared therefrom, allmixing units usable customarily for the seed dressing are useful.Specifically, the procedure in seed dressing is to place the seed into amixer in batchwise or continuous operation, to add the particulardesired amount of seed-dressing formulations, either as such or afterprior dilution with water, and to mix until the formulation isdistributed homogeneously on the seed. If appropriate, this is followedby a drying operation.

The application rate of the seed-dressing formulations usable inaccordance with the invention can be varied within a relatively widerange. It is guided by the particular content of the compounds of theformula (I) in the formulations and by the seed. The application ratesof the compound of the formula (I) are generally between 0.001 and 50 gper kilogram of seed, preferably between 0.01 and 15 g per kilogram ofseed.

Animal Health

In the field of animal health, i.e. in the field of veterinary medicine,the compounds of the formula (I) are active against animal parasites, inparticular ectoparasites or endoparasites. The term “endoparasites”includes especially helminths and protozoans, such as coccidia.Ectoparasites are typically and preferably arthropods, especiallyinsects and acarids.

In the field of veterinary medicine, the compounds of the formula (I)having favourable toxicity to warm-blooded species are suitable forcontrolling parasites which occur in animal breeding and animalhusbandry in livestock, breeding animals, zoo animals, laboratoryanimals, experimental animals and domestic animals They are activeagainst all or specific stages of development of the parasites.

Agricultural livestock include, for example, mammals such as sheep,goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer,and particularly cattle and pigs; poultry such as turkeys, ducks, geese,and particularly chickens; fish and crustaceans, for example inaquaculture, and also insects such as bees.

Domestic animals include, for example, mammals, such as hamsters, guineapigs, rats, mice, chinchillas, ferrets, and particularly dogs, cats,caged birds, reptiles, amphibians and aquarium fish.

In a preferred embodiment, the compounds of the formula (I) areadministered to mammals.

In another preferred embodiment, the compounds of the formula (I) areadministered to birds, namely caged birds and particularly poultry.

Use of the compounds of the formula (I) for the control of animalparasites is intended to reduce or prevent illness, cases of death andreductions in performance (in the case of meat, milk, wool, hides, eggs,honey and the like), such that more economical and simpler animalkeeping is enabled and better animal well-being is achievable.

In relation to the field of animal health, the term “control” or“controlling” means that the compounds of the formula (I) are effectivein reducing the incidence of the particular parasite in an animalinfected with such parasites to an innocuous degree. More specifically,“controlling” in the present context means that the compound of theformula (I) can kill the respective parasite, inhibit its growth, orinhibit its proliferation.

Arthropods Include:

from the order of the Anoplurida, for example Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; fromthe order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.; from the order of the Diptera and thesuborders Nematocerina and Brachycerina, for example Aedes spp.,Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomusspp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp.,Wilhelmia spp., Hybomitra spp., Aty lotus spp., Tabanus spp.,Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaeaspp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp.,Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.,Rhinoestrus spp., Tipula spp.; from the order of the Siphonapterida, forexample Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp.,Ceratophyllus spp.;

from the order of the Heteropterida, for example Cimex spp., Triatomaspp., Rhodnius spp., Panstrongylus spp.; and also nuisance and hygienepests from the order of the Blattarida.

Arthropods further include:

from the subclass of the Acari (Acarina) and the order of theMetastigmata, for example from the family of Argasidae like Argas spp.,Ornithodorus spp., Otobius spp., from the family of Ixodidae like Ixodesspp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (the originalgenus of multi-host ticks); from the order of Mesostigmata likeDermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietiaspp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.;from the order of the Actinedida (Prostigmata), for example Acarapisspp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergatesspp., Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorusspp.; and from the order of the Acaridida (Astigmata), for exampleAcarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp.,Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp.,Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp.,Laminosioptes spp.

Parasitic Protozoa Include:

Mastigophora (Flagellata), for example Trypanosomatidae, for example,Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense,T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T.vivax, Leishmania brasiliensis, L. donovani, L. tropica, for exampleTrichomonadidae, for example, Giardia lamblia, G. canis;

Sarcomastigophora (Rhizopoda) such as Entamoebidae, for example,Entamoeba histolytica, Hartmanellidae, for example, Acanthamoeba sp.,Harmanella sp.;

Apicomplexa (Sporozoa) such as Eimeridae, for example, Eimeriaacervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E.arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E. canis, E.chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E.debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E.flavescens, E. gallopavonis, E. hagani, E. intestinalis, E. iroquoina,E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E. media,E. meleagridis, E. meleagrimitis, E. mitis, E. necatrix, Eninakohlyakimovae, E. ovis, E. parva, E. pavonis, E. perforans, E.phasani, E. piriformis, E. praecox, E. residua, E. scabra, E. spec., E.stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuernii,Globidium spec., Isospora belli, I. canis, I. felis, I. ohioensis, I.rivolta, I. spec., I. suis, Cystisospora spec., Cryptosporidium spec.,in particular C. parvum; such as Toxoplasmadidae, for example Toxoplasmagondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; suchas Sarcocystidae, for example Sarcocystis bovicanis, S. bovihominis, S.ovicanis, S. ovifelis, S. neurona, S. spec., S. suihominis, such asLeucozoidae, for example Leucozytozoon simondi, such as Plasmodiidae,for example Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P.vivax, P. spec., such as Piroplasmea, for example Babesia argentina, B.bovis, B. canis, B. spec., Theileria parva, Theileria spec., such asAdeleina, for example Hepatozoon canis, H. spec.

Pathogenic endoparasites which are helminths include Platyhelmintha(e.g. Monogenea, cestodes and trematodes), nematodes, Acanthocephala,and Pentastoma. These include:

Monogenea: for example: Gyrodactylus spp., Dactylogyrus spp., Polystomaspp.;

Cestodes: from the order of the Pseudophyllidea for example:Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligulaspp., Bothridium spp., Diplogonoporus spp.;

from the order of the Cyclophyllida, for example: Mesocestoides spp.,Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosomaspp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaeniaspp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp.,Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp.,Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp.,Joyeuxiella spp., Diplopylidium spp.;

Trematodes: from the class of the Digenea, for example: Diplostomumspp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp.,Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp.,Leucochloridium spp., Brachylaima spp., Echinostoma spp.,Echinoparyphium spp., Echinochasmus spp., Hyporaeum spp., Fasciola spp.,Fasciolides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelumspp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp.,Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp., Notocotylusspp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp.,Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp.,Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp.,Metorchis spp., Heterophyes spp., Metagonimus spp.;

Nematodes: Trichinellida, for example Trichuris spp., Capillaria spp.,Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinellaspp.; p From the order of the Tylenchida, for example: Micronema spp.,Strongyloides spp.;

from the order of the Rhabditida, for example: Strongylus spp.,Triodontophorus spp., Oesophagodontus spp., Trichonema spp.,Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp.,Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp.,Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp.,Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp.,Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muelleriusspp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp.,Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp.,Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerusspp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp.,Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagiaspp., Teladorsagia spp., Marshallagia spp., Cooperia spp.,Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp.,Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.;

From the order of the Spirurida, for example: Oxyuris spp., Enterobiusspp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.;Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp.,Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp.,Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp.,Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp.,Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoidesspp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp.;

Acanthocephala: from the order of the Oligacanthorhynchida, for example:Macracanthorhynchus spp., Prosthenorchis spp.; from the order of thePolymorphida, for example Filicollis spp.; from the order of theMoniliformida, for example Moniliformis spp.;

From the order of the Echinorhynchida, for example, Acanthocephalusspp., Echinorhynchus spp., Leptorhynchoides spp.;

Pentastoma: from the order of the Porocephalida, for example, Linguatulaspp.

In the veterinary field and in animal keeping, the compounds of theformula (I) are administered by methods generally known in the art, suchas via the enteral, parenteral, dermal or nasal route in the form ofsuitable preparations. Administration may be prophylactic ortherapeutic.

Thus, one embodiment of the present invention refers to the use of acompound of the formula (I) as a medicament.

A further aspect refers to the use of a compound of the formula (I) asan antiendoparasitic agent, in particular a helminthicidal agent orantiprotozoic agent. Compounds of the formula (I) are suitable for useas an antiendoparasitic agent, especially as a helminthicidal agent orantiprotozoic agent, for example in animal breeding, in animalhusbandry, in animal houses and in the hygiene sector.

A further aspect in turn relates to the use of a compound of the formula(I) as an antiectoparasitic, in particular an arthropodicide such as aninsecticide or an acaricide. A further aspect relates to the use of acompound of the formula (I) as an antiectoparasitic, in particular anarthropodicide such as an insecticide or an acaricide, for example inanimal husbandry, in animal breeding, in animal houses or in the hygienesector.

Vector Control

The compounds of the formula (I) can also be used in vector control. Inthe context of the present invention, a vector is an arthropod,especially an insect or arachnid, capable of transmitting pathogens, forexample, viruses, worms, single-cell organisms and bacteria, from areservoir (plant, animal, human, etc.) to a host. The pathogens can betransmitted either mechanically (for example trachoma by non-stingingflies) to a host or after injection (for example malaria parasites bymosquitoes) into a host.

Examples of vectors and the diseases or pathogens they transmit are:

1) Mosquitoes

-   -   Anopheles: malaria, filariasis;    -   Culex: Japanese encephalitis, filariasis, other viral diseases,        transmission of worms;    -   Aedes: yellow fever, dengue fever, filariasis, other viral        diseases;    -   Simulidae: transmission of worms, in particular Onchocerca        volvulus;

2) Lice: skin infections, epidemic typhus;

3) Fleas: plague, endemic typhus;

4) Flies: sleeping sickness (trypanosomiasis); cholera, other bacterialdiseases;

5) Mites: acariosis, epidemic typhus, rickettsialpox, tularaemia, SaintLouis encephalitis, tick-borne encephalitis (TBE), Crimean-Congohaemorrhagic fever, borreliosis;

6) Ticks: borellioses such as Borrelia duttoni, tick-borne encephalitis,Q fever (Coxiella burnetii), babesioses (Babesia canis canis).

Examples of vectors in the context of the present invention are insects,for example aphids, flies, leafhoppers or thrips, which can transmitplant viruses to plants. Other vectors capable of transmitting plantviruses are spider mites, lice, beetles and nematodes.

Further examples of vectors in the context of the present invention areinsects and arachnids such as mosquitoes, especially of the generaAedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A.dims (malaria) and Culex, lice, fleas, flies, mites and ticks, which cantransmit pathogens to animals and/or humans

Vector control is also possible if the compounds of the formula (I) areresistance-breaking.

Compounds of the formula (I) are suitable for use in the prevention ofdiseases and/or pathogens transmitted by vectors. Thus, a further aspectof the present invention is the use of compounds of the formula (I) forvector control, for example in agriculture, in horticulture, inforestry, in gardens and in leisure facilities, and also in theprotection of materials and stored products.

Protection of Industrial Materials

The compounds of the formula (I) are suitable for protecting industrialmaterials against attack or destruction by insects, for example from theorders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera andZygentoma.

Industrial materials in the present context are understood to meaninanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions. The use of the invention for protection of wood isparticularly preferred.

In a further embodiment, the compounds of the formula (I) are usedtogether with at least one further insecticide and/or at least onefungicide.

In a further embodiment, the compounds of the formula (I) are present asa ready-to-use pesticide, i.e. they can be applied to the material inquestion without further modifications. Suitable further insecticides orfungicides are in particular those mentioned above.

Surprisingly, it has also been found that the compounds of the formula(I) can be employed for protecting objects which come into contact withsaltwater or brackish water, in particular hulls, screens, nets,buildings, moorings and signalling systems, against fouling. It isequally possible to use the compounds of the formula (I), alone or incombinations with other active compounds, as antifouling agents.

Control of Animal Pests in the Hygiene Sector

The compounds of the formula (I) are suitable for controlling animalpests in the hygiene sector. More particularly, the invention can beused in the domestic sector, in the hygiene sector and in the protectionof stored products, particularly for control of insects, arachnids andmites encountered in enclosed spaces, for example dwellings, factoryhalls, offices, vehicle cabins. For controlling animal pests, thecompounds of the formula (I) are used alone or in combination with otheractive compounds and/or auxiliaries. They are preferably used indomestic insecticide products. The compounds of the formula (I) areeffective against sensitive and resistant species, and against alldevelopmental stages.

These pests include, for example, pests from the class Arachnida, fromthe orders Scorpiones, Araneae and Opiliones, from the classes Chilopodaand Diplopoda, from the class Insecta the order Blattodea, from theorders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera,Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria orOrthoptera, Siphonaptera and Zygentoma and from the class Malacostracathe order Isopoda.

Application is effected, for example, in aerosols, unpressurized sprayproducts, for example pump and atomizer sprays, automatic foggingsystems, foggers, foams, gels, evaporator products with evaporatortablets made of cellulose or plastic, liquid evaporators, gel andmembrane evaporators, propeller-driven evaporators, energy-free, orpassive, evaporation systems, moth papers, moth bags and moth gels, asgranules or dusts, in baits for spreading or in bait stations.

Elucidation of the Processes and Intermediates

The preparation and use examples which follow illustrate the inventionwithout limiting it. The products were characterized by 1H NMRspectroscopy and/or LC/MS (liquid chromatography mass spectrometry).

The log P values were determined in accordance with OECD Guideline 117(EC Directive 92/69/EEC) by HPLC (high-performance liquidchromatography) using reversed-phase (RP) columns (C18), by thefollowing methods:

[a] The LC-MS determination in the acidic range was effected at pH 2.7with 0.1% aqueous formic acid and acetonitrile (contains 0.1% formicacid) as eluents; linear gradient from 10% acetonitrile to 95%acetonitrile.

[b] LC-MS determination in the neutral range was effected at pH 7.8 with0.001 molar aqueous ammonium hydrogencarbonate solution and acetonitrileas eluents; linear gradient from 10% acetonitrile to 95% acetonitrile.

Calibration was effected with unbranched alkan-2-ones (having 3 to 16carbon atoms) with known log P values (log P values determined on thebasis of the retention times by linear interpolation between twosuccessive alkanones).

The NMR spectra were determined with a Bruker Avance 400 fitted with aflow probe head (volume 60 μl). In individual cases, the NMR spectrawere measured with a Bruker Avance II 600.

The 1H NMR data of selected examples are stated in the form of 1H NMRpeak lists. For each signal peak, first the δ value in ppm and then thesignal intensity in round brackets are listed. The δ value signalintensity—number pairs for different signal peaks are listed withseparation from one another by semicolons.

The peak list for one example therefore takes the form of:

δ₁ (intensity 1); δ₂ (intensity 2); . . . ; δ_(i) (intensity i); . . . ;δ_(n) (intensity n)

The intensity of sharp signals correlates with the height of the signalsin a printed example of an NMR spectrum in cm and shows the true ratiosof the signal intensities. In the case of broad signals, several peaksor the middle of the signal and the relative intensity thereof may beshown in comparison to the most intense signal in the spectrum.

For calibration of the chemical shift of the 1H NMR spectra we usetetramethylsilane and/or the chemical shift of the solvent, particularlyin the case of spectra measured in DMSO. Therefore, thetetramethylsilane peak may but need not occur in NMR peak lists.

The lists of the 1H NMR peaks are similar to the conventional 1H NMRprintouts and thus usually contain all peaks listed in a conventionalNMR interpretation.

In addition, like conventional 1H NMR printouts, they may show solventsignals, signals of stereoisomers of the target compounds, whichlikewise form part of the subject matter of the invention, and/or peaksof impurities.

In the reporting of compound signals in the delta range of solventsand/or water, our lists of 1H NMR peaks show the usual solvent peaks,for example peaks of DMSO in DMSO-D6 and the peak of water, whichusually have a high intensity on average.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities usually have a lower intensity on average than the peaks ofthe target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help in this case to identifyreproduction of our preparation process with reference to “by-productfingerprints”.

An expert calculating the peaks of the target compounds by known methods(MestreC, ACD simulation, but also with empirically evaluated expectedvalues) can, if required, isolate the peaks of the target compounds,optionally using additional intensity filters. This isolation would besimilar to the relevant peak picking in conventional 1H NMRinterpretation.

Further details of 1H NMR peak lists can be found in Research DisclosureDatabase Number 564025.

Synthesis of Compounds of the Formula (I) by Process A

Preparation Example 1:6-Isopropyl-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one (1)Step 1: 4-Amino-N-isopropyl-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-1)

Under argon, 3 ml of a 2M trimethylaluminium solution (6.02 mmol) intoluene were slowly added dropwise to 356 mg (6.02 mmol) ofisopropylamine in 1,2-dichloroethane and the mixture was stirred at roomtemperature for 30 min 500 mg (2.00 mmol) of ethyl4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate (III-1) were thenadded, and the reaction mixture was subsequently heated under refluxovernight. After cooling, the reaction mixture was carefully dischargedinto a 10% potassium sodium tartrate solution (about 100 ml). Themixture was extracted three times with dichloromethane, and the combinedorganic phases were dried over sodium sulphate, filtered andconcentrated. The residue was stirred with a little acetonitrile to givea suspension. The insoluble portion was filtered off with suction anddried under reduced pressure. This gave 340 mg (99% pure, 63.9% oftheory) of the title compound (II-1).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.046(2.3); 9.042(2.4); 8.704(1.8);8.700(2.0); 8.692(2.0); 8.688(1.9); 8.218(1.0); 8.214(1.4); 8.208(1.0);8.198(1.2); 8.194(1.5); 8.193(1.5); 8.188(1.1); 7.639(1.3); 7.620(1.3);7.581(1.4); 7.579(1.4); 7.569(1.4); 7.567(1.4); 7.561(1.4); 7.559(1.3);7.549(1.3); 7.547(1.3); 6.982(4.0); 4.077(0.7); 4.061(1.0); 4.042(1.0);4.025(0.7); 3.904(0.9); 3.338(73.4); 2.526(0.6); 2.513(11.6);2.509(23.1); 2.504(30.0); 2.500(21.6); 2.495(10.5); 1.143(16.0);1.126(15.8); 0.000(7.2); −0.008(0.3)

Step 2:6-Isopropyl-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one (1)

300 mg (1.14 mmol) of4-amino-N-isopropyl-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide (II-1)were initially charged in N,N-dimethylacetamide. 98 mg (0.57 mmol) ofp-toluenesulphonic acid and 339 mg (2.29 mmol) of triethyl orthoformatewere added thereto and the reaction mixture was heated at 130° C. in aCEM Discover microwave at 200 watts for 1 h. The cooled reaction mixturewas concentrated under reduced pressure, and the residue was trituratedwith acetonitrile and the solid was filtered off. The filtrate was thenconcentrated and purified chromatographically by MPLC on an RP(C-18)column. This gave 25 mg (96% pure, 7.6% of theory) of the title compound(1).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.307(2.2); 9.302(2.2); 8.814(1.6);8.811(1.7); 8.802(1.7); 8.799(1.7); 8.734(6.2); 8.516(1.0); 8.512(1.3);8.506(1.0); 8.496(1.1); 8.491(1.4); 8.486(1.0); 8.144(3.9); 7.659(1.3);7.647(1.3); 7.641(1.3); 7.639(1.3); 7.628(1.2); 7.627(1.2); 5.054(0.4);5.037(1.1); 5.019(1.5); 5.002(1.1); 4.985(0.4); 3.337(1.4); 2.526(0.8);2.513(17.3); 2.508(34.7); 2.504(45.2); 2.499(32.4); 2.495(15.5);1.483(16.0); 1.466(15.8); 1.142(0.4); 1.126(0.4); 0.000(8.5)

Preparation Example 2:6-Isobutyl-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one (3)Step 1: 4-Amino-N-isobutyl-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide((II-3))

1.75 g (7.02 mmol) of ethyl4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate (III-1) wereinitially charged in ethanol, and 1.97 g of potassium hydroxide (35.10mmol), dissolved in ethanol, were added. The reaction mixture wasstirred at 50° C. overnight and then concentrated to dryness. Theresidue was suspended in a little water and the product was precipitatedwith 10% strength aqueous citric acid solution. The insoluble fractionwas filtered off with suction and dried well under reduced pressure. Theresulting 4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylic acid (1.32g, 100% pure, 85.0% of theory) was directly reacted further.

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.112(1.2); 9.108(1.4); 9.099(0.7);9.086(15.3); 9.085(15.4); 9.080(16.0); 9.018(0.3); 9.012(0.4);8.730(1.2); 8.727(1.2); 8.719(1.4); 8.715(1.4); 8.701(13.6);8.697(14.4); 8.689(14.5); 8.685(14.2); 8.607(0.4); 8.603(0.4);8.595(0.4); 8.297(0.7); 8.292(0.9); 8.287(0.8); 8.277(0.9); 8.271(1.2);8.262(8.1); 8.258(10.9); 8.253(8.0); 8.242(8.7); 8.238(11.2);8.233(8.1); 7.580(1.0); 7.566(1.5); 7.560(11.6); 7.558(11.0);7.548(11.5); 7.546(10.9); 7.540(10.5); 7.538(9.8); 7.528(10.0);7.526(9.3); 7.506(0.4); 7.494(0.4); 7.486(0.4); 7.473(0.4); 7.133(1.1);6.917(1.6); 6.028(1.3); 4.271(0.9); 4.253(2.8); 4.235(2.8); 4.218(0.9);3.578(0.4); 3.545(0.5); 3.466(1.1); 3.448(1.5); 3.431(1.8); 3.324(25.6);3.120(0.5); 3.092(0.4); 2.951(0.3); 2.675(2.3); 2.671(3.1); 2.667(2.3);2.555(5.6); 2.541(2.3); 2.524(9.2); 2.517(30.9); 2.511(156.3);2.506(313.9); 2.502(413.1); 2.497(295.7); 2.493(141.3); 2.481(18.0);2.443(5.2); 2.338(1.1); 2.333(2.2); 2.329(3.0); 2.324(2.2); 2.290(0.4);1.909(0.8); 1.295(3.0); 1.277(6.4); 1.260(3.0); 1.073(0.8); 1.055(1.5);1.038(0.7); 0.146(1.3); 0.008(11.0); 0.000(302.5); −0.009(11.0);−0.150(1.3)

100 mg (0.45 mmol) of this4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylic acid were theninitially charged in toluene. 376 mg (3.16 mmol) of thionyl chloridewere added and the reaction mixture was heated under reflux for 3 hours.After cooling, the reaction was concentrated under reduced pressure anddried under high vacuum. The acid chloride obtained in this manner wastaken up in acetonitrile and added to a solution of 88 mg (0.68 mmol) ofN,N-diisopropylethylamine and 36.36 mg (0.50 mmol) of isobutylamine inacetonitrile. The reaction mixture was then stirred at room temperatureovernight. After evaporation of the solvent the residue was taken up inethyl acetate and saturated sodium chloride solution. The organic phasewas separated off, dried over sodium sulphate and concentrated. Thisgave 71 mg (84% pure, 47.7% of theory) of the title compound (II-3)which were converted directly further into (3) in Step 2.

LC-MS: mass found [m/z]=276.10

Step 2:6-Isobutyl-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one (3)

71 mg (0.22 mmol; 84% pure) of4-amino-N-isobutyl-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide (II-3)were initially charged in 266 mg (3.05 mmol) of N,N-dimethylacetamide. 2mg (0.013 mmol) of p-toluenesulphonic acid and 57 mg (0.39 mmol) oftriethyl orthoformate were added and the reaction mixture was heated at120° C. in a CEM Discover microwave at 200 watts for 10 min. The cooledreaction mixture was concentrated and purified chromatographically. Thisgave 24 mg (90% pure, 34.3% of theory) of the title compound (3).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.302(2.1); 9.297(2.1); 9.049(0.4);9.044(0.4); 8.815(1.8); 8.811(1.9); 8.803(1.8); 8.799(1.8); 8.703(0.3);8.699(0.4); 8.691(0.4); 8.687(0.4); 8.634(6.2); 8.510(1.1); 8.506(1.4);8.500(1.1); 8.490(1.1); 8.486(1.4); 8.484(1.4); 8.480(1.1); 7.662(1.3);7.660(1.4); 7.650(1.3); 7.648(1.3); 7.642(1.3); 7.640(1.3); 7.630(1.2);7.628(1.3); 6.974(0.7); 3.895(4.7); 3.876(4.7); 3.323(24.1); 3.022(0.4);3.005(0.6); 2.990(0.4); 2.512(10.6); 2.508(21.2); 2.503(27.9);2.499(20.3); 2.495(10.0); 2.162(0.4); 2.145(0.8); 2.128(1.0);2.111(0.9); 2.093(0.4); 0.916(16.0); 0.899(15.5); 0.873(3.2);0.856(3.1); 0.008(0.3); 0.000(8.4); −0.008(0.3)

Preparation Example 3:2-(Pyridin-3-yl)-6-(2,2,2-trifluoroethyl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(5) Step 1:4-Amino-2-(pyridin-3-yl)-N-(2,2,2-trifluoroethyl)-1,3-thiazole-5-carboxamide(II-5)

Under argon, 3 ml of a 2M trimethylaluminium solution (6.02 mmol) intoluene were slowly added dropwise to 596 mg (6.02 mmol) of2,2,2-trifluoroethylamine in 1,2-dichloroethane, and the mixture wasstirred at room temperature for 30 min 500 mg (2.0 mmol) of ethyl4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate (III-1) were thenadded, and the reaction mixture was subsequently heated under refluxovernight. After cooling, the reaction mixture was carefully dischargedinto a 10% potassium sodium tartrate solution (about 100 ml). Themixture was extracted three times with methylene chloride, and theorganic phase was removed, dried over sodium sulphate, filtered andconcentrated. The residue was stirred with a little acetonitrile to givea suspension. The insoluble portion was filtered off with suction anddried under reduced pressure. This gave 299 mg (91% pure, 44.8% oftheory) of the title compound (II-5).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.114(0.8); 9.110(0.8); 9.074(9.3);9.070(9.3); 8.728(7.9); 8.724(7.8); 8.716(8.3); 8.712(7.5); 8.476(3.0);8.461(6.3); 8.446(3.0); 8.318(0.4); 8.298(0.4); 8.293(0.5); 8.288(0.4);8.277(0.4); 8.272(0.5); 8.268(0.5); 8.249(4.1); 8.245(5.6); 8.240(4.0);8.229(4.5); 8.225(5.8); 8.224(5.8); 8.220(4.1); 7.594(5.4); 7.593(5.3);7.582(5.6); 7.580(5.7); 7.574(5.3); 7.573(5.1); 7.562(5.2); 7.560(5.2);7.548(0.5); 7.164(16.0); 5.759(1.8); 4.272(0.5); 4.254(1.5); 4.236(1.5);4.218(0.5); 4.040(1.7); 4.016(5.6); 4.000(5.7); 3.992(6.1); 3.976(5.5);3.968(2.4); 3.952(1.9); 3.905(2.0); 3.332(49.0); 2.678(0.5); 2.673(0.6);2.669(0.4); 2.509(72.6); 2.504(92.8); 2.500(67.2); 2.335(0.5);2.331(0.6); 2.327(0.4); 1.296(1.6); 1.279(3.2); 1.261(1.5); 0.008(2.8);0.000(58.8); −0.008(2.6)

Step 2:2-(Pyridin-3-yl)-6-(2,2,2-trifluoroethyl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(5)

240 mg (0.79 mmol) of4-amino-2-(pyridin-3-yl)-N-(2,2,2-trifluoroethyl)-1,3-thiazole-5-carboxamide(II-5) were initially charged in 3 ml of N,N-dimethylacetamide. 68 mg(0.40 mmol) of p-toluenesulphonic acid and 235 mg (1.59 mmol) oftriethyl orthoformate were added thereto and the reaction mixture washeated at 130° C. in a CEM Discover microwave at 200 watts for 1 h. Thecooled reaction mixture was concentrated under reduced pressure, and theresidue was triturated with acetonitrile and the solid was filtered off.The solid was then purified by MPLC on an RP(C-18) column. This gave 69mg (92% pure, 25.6% of theory) of the title compound (5).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.320(8.2); 9.315(8.2); 9.302(0.4);8.829(6.4); 8.825(6.8); 8.817(6.9); 8.813(6.6); 8.698(16.0); 8.530(4.0);8.526(5.1); 8.520(3.9); 8.510(4.3); 8.506(5.3); 8.505(5.3); 8.500(4.0);8.318(0.4); 7.672(4.8); 7.671(4.8); 7.660(4.8); 7.659(4.7); 7.652(4.8);7.651(4.6); 7.640(4.5); 7.639(4.4); 5.143(0.3); 5.121(0.4); 5.089(3.5);5.067(11.4); 5.044(11.9); 5.021(4.0); 3.363(0.6); 3.336(289.1);2.720(1.5); 2.678(0.6); 2.674(0.8); 2.669(0.6); 2.527(2.1); 2.513(48.7);2.509(96.7); 2.505(125.4); 2.500(89.6); 2.496(42.7); 2.336(0.6);2.331(0.8); 2.327(0.6); 2.077(0.4); 0.008(1.2); 0.000(30.0); −0.008(1.1)

Preparation Example 4:6-(3-Methoxyphenyl)-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(10) Step 1:4-Amino-N-(3-methoxyphenyl)-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-10)

Under argon, 1.8 ml of a 2M trimethylaluminium solution (3.61 mmol) intoluene were slowly added dropwise to 445 mg (3.61 mmol) of 3-methoxyaniline in 1,2-dichloroethane and the mixture was stirred at roomtemperature for 1 h. 300 mg (1.2 mmol) of ethyl4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate (III-1) were thenadded, and the reaction mixture was subsequently heated under refluxovernight. After cooling, the reaction mixture was carefully dischargedinto a 10% potassium sodium tartrate solution (about 120 ml). Themixture was extracted three times with methylene chloride, and thecombined organic phases were dried over sodium sulphate, filtered andconcentrated. The residue was stirred with a little acetonitrile to givea suspension. The insoluble portion was filtered off with suction anddried under reduced pressure. This gave 120 mg (96% pure, 29.3% oftheory) of the title compound (II-10).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.618(2.9); 9.113(0.4); 9.107(0.5);9.099(2.3); 9.093(2.3); 8.736(1.5); 8.732(1.7); 8.724(1.7); 8.720(1.7);8.271(1.0); 8.266(1.5); 8.261(0.9); 8.251(0.8); 8.246(1.4); 8.241(0.9);7.607(1.3); 7.595(1.3); 7.587(1.3); 7.575(1.4); 7.361(1.4); 7.355(2.5);7.350(1.7); 7.303(1.0); 7.282(1.7); 7.238(3.5); 7.232(3.1); 7.211(2.7);7.191(1.2); 6.658(1.2); 6.652(1.2); 6.638(1.1); 6.631(1.1); 4.253(0.7);4.235(0.7); 3.747(16.0); 3.330(15.3); 2.525(0.6); 2.507(25.7);2.503(34.3); 2.499(26.3); 2.076(0.7); 1.295(0.8); 1.278(1.5);1.260(0.7); 0.008(1.5); 0.007(1.5); 0.000(44.0); −0.008(1.9)

Step 2:6-(3-Methoxyphenyl)-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(10)

100 mg (0.29 mmol) of4-amino-N-(3-methoxyphenyl)-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-10) were initially charged in N,N-dimethylacetamide. 25 mg (0.15mmol) of p-toluenesulphonic acid and 87 mg (0.59 mmol) of triethylorthoformate were added thereto and the reaction mixture was heated at130° C. in a CEM Discover microwave at 200 watts for 1 h. Water wasadded to the cooled reaction mixture which was then extracted repeatedlywith dichloromethane. The combined organic phases were dried over sodiumsulfate, filtered and concentrated. The residue was then purified byMPLC column chromatography. This gave 20 mg (100% pure, 20.2% of theory)of the title compound (10).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.345(0.5); 9.340(0.5); 8.833(0.4);8.829(0.4); 8.821(0.4); 8.817(0.4); 8.620(1.4); 7.495(0.6); 7.475(0.4);7.217(0.3); 7.211(0.6); 7.206(0.4); 7.155(0.4); 7.134(0.5); 3.818(3.8);3.328(15.7); 2.944(16.0); 2.784(13.5); 2.507(16.3); 2.502(21.3);2.498(16.0); 1.957(14.1); 0.008(1.0); 0.000(24.1); −0.008(1.1)

Preparation Example 5:6-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(22) Step 1:4-Amino-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-21)

Under argon, 1.5 ml of a 2M trimethylaluminium solution (3.01 mmol) intoluene were slowly added dropwise to 720 mg (3.01 mmol) of2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]aniline in1,2-dichloroethane, and the mixture was stirred at room temperature for30 min. 250 mg (1.00 mmol) of ethyl4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate (III-1) were thenadded, and the reaction mixture was subsequently heated under refluxovernight. After cooling, the reaction mixture was carefully dischargedinto a 10% potassium sodium tartrate solution (about 200 ml). Themixture was extracted three times with methylene chloride, and thecombined organic phases were dried over sodium sulphate, filtered andconcentrated. The residue was stirred with a little acetonitrile to givea suspension. The insoluble portion was filtered off with suction anddried under reduced pressure. This gave 144 mg (92% pure, 29.9% oftheory) of the title compound (II-21).

1H-NMR (601.6 MHz, d₆-DMSO): δ=9.566(4.6); 9.110(0.4); 9.100(3.4);9.096(3.4); 8.737(2.4); 8.734(2.6); 8.729(2.8); 8.726(2.8); 8.270(1.3);8.267(1.9); 8.264(1.3); 8.257(1.3); 8.254(2.0); 8.251(1.3); 7.696(2.8);7.683(2.8); 7.601(1.7); 7.594(1.7); 7.588(1.7); 7.580(1.6); 7.268(2.5);7.250(2.5); 7.209(5.5); 4.250(0.6); 4.238(0.6); 3.891(1.1); 3.874(3.4);3.857(3.5); 3.840(1.2); 3.343(61.4); 2.616(0.4); 2.507(51.6);2.504(70.6); 2.501(53.2); 2.406(16.0); 1.290(0.6); 1.278(1.2);1.266(0.6); 0.005(1.5); 0.000(41.7)

Step 2:6-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(21)

120 mg (0.27 mmol) of4-amino-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-21) were initially charged in N,N-dimethylacetamide. 23 mg (0.14mmol) of p-toluenesulphonic acid and 80 mg (0.54 mmol) of triethylorthoformate were added thereto and the reaction mixture was heated at130° C. in a CEM Discover microwave at 200 watts for 1 h. The cooledreaction mixture was concentrated under reduced pressure, and theresidue was triturated with acetonitrile and the product was filteredoff as a solid. The filtrate was then concentrated and purifiedchromatographically by MPLC on an RP(C-18) column. This gave, in total,43 mg (98% pure, 34.3% of theory) of the title compound (21).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.350(3.0); 9.346(3.1); 9.344(3.0);8.839(2.4); 8.836(2.6); 8.827(2.6); 8.824(2.6); 8.679(8.7); 8.561(1.4);8.557(1.8); 8.551(1.4); 8.541(1.5); 8.537(1.9); 8.535(1.9); 8.531(1.5);7.939(3.1); 7.921(3.1); 7.684(1.8); 7.683(1.7); 7.672(1.7); 7.671(1.7);7.664(1.8); 7.663(1.7); 7.652(1.7); 7.651(1.7); 7.518(2.7); 7.491(2.6);4.062(1.2); 4.037(3.9); 4.011(4.0); 3.985(1.4); 3.330(57.6); 2.945(1.0);2.785(0.7); 2.672(0.4); 2.526(1.0); 2.512(19.8); 2.508(40.6);2.503(53.8); 2.499(39.4); 2.494(19.5); 2.471(16.0); 2.330(0.3);2.076(10.9); 1.958(0.8); 0.008(1.0); 0.000(30.1); −0.009(1.2)

Step 3—Main Product:6-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(22)

At 0° C., 19.18 mg (70% strength, 0.08 mmol) of meta-chloroperbenzoicacid were added to a solution of 32.0 mg (0.07 mmol) of6-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(21) in 3 ml of dichloromethane. The reaction mixture was stirred atroom temperature for 2 hours, and saturated sodium carbonate solutionwas then added. After 20 minutes, the phases were separated, the aqueousphase was extracted two more times with dichloromethane and the combinedorganic phases were dried over sodium sulphate After evaporation of thesolvent, the residue was then purified chromatographically by MPLC on anRP(C-18) column. This gave 10 mg (95% pure, 28.1% of theory) of thetitle compound (22).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.761(0.5); 9.353(6.6); 9.347(6.9);9.102(0.4); 8.836(5.2); 8.828(4.9); 8.824(5.2); 8.738(0.5); 8.723(15.6);8.557(4.0); 8.553(2.9); 8.543(2.8); 8.537(4.3); 8.533(3.1); 8.315(2.5);8.195(6.5); 8.176(6.5); 8.039(0.4); 7.951(2.4); 7.685(3.8); 7.673(3.8);7.665(4.0); 7.653(3.8); 7.635(5.0); 7.608(5.1); 7.366(0.4); 7.238(0.6);5.755(1.0); 4.293(0.9); 4.271(1.2); 4.263(1.3); 4.233(1.1); 4.182(0.4);4.124(1.0); 4.100(1.2); 3.505(1.6); 3.322(748.9); 2.944(1.9);2.891(16.0); 2.784(1.6); 2.731(14.3); 2.716(0.5); 2.670(6.0);2.666(4.8); 2.505(695.9); 2.501(960.0); 2.497(767.5); 2.395(0.8);2.373(2.4); 2.328(6.2); 2.324(5.1); 2.283(0.4); 1.957(1.9); 1.303(0.3);1.284(0.6); 1.233(2.0); 0.854(0.4); 0.146(3.0); 0.008(21.8);0.000(638.0); −0.078(0.4); −0.150(3.2)

Step 3—Minor Product:6-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-2-(1-oxidopyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(23)

In the course of the preparation of the compound (23) according to “Step3—main product”, compound (23) was simultaneously insulated as minorproduct. This gave 11 mg (94% pure, 30.5% of theory) of the titlecompound (23).

1H-NMR (400.0 MHz, d₆-DMSO): δ=8.928(9.2); 8.734(16.0); 8.463(5.2);8.446(5.3); 8.315(0.9); 8.196(7.0); 8.177(7.1); 8.082(5.1); 8.061(5.7);7.668(4.5); 7.649(5.9); 7.633(8.7); 7.608(5.6); 7.573(0.4); 7.251(0.4);4.265(1.6); 4.236(1.3); 4.117(1.2); 4.106(1.2); 4.092(1.4);3.322(182.5); 2.671(2.1); 2.502(339.3); 2.498(298.4); 2.402(0.7);2.373(1.6); 2.329(2.4); 0.146(1.6); 0.000(312.8); −0.083(0.4);−0.150(1.7)

Preparation Example 6:2-(Pyridin-3-yl)-6-[3-(trifluoromethyl)benzyl][1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(28) Step 1:4-Amino-2-(pyridin-3-yl)-N-[3-(trifluoromethyl)benzyl]-1,3-thiazole-5-carboxamide(II-28)

Under argon, 2.4 ml of a 2M trimethylaluminium solution (4.81 mmol) intoluene were slowly added dropwise to 843 mg (4.81 mmol) of3-(trifluoromethyl)benzylamine in 20 ml of 1,2-dichloroethane, and themixture was stirred at room temperature for 30 min 400 mg (1.61 mmol) ofethyl 4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate (III-1) werethen added, and the reaction mixture was subsequently heated underreflux overnight. After cooling, the reaction mixture was carefullydischarged into a 10% potassium sodium tartrate solution (about 120 ml).The mixture was extracted three times with dichloromethane, and thecombined organic phases were dried over sodium sulphate, filtered andconcentrated. The residue was stirred with a little n-pentane to give asuspension. The insoluble portion was filtered off with suction anddried under reduced pressure. This gave 425 mg (100% pure, 70.0% oftheory) of the title compound (II-28).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.063(9.1); 9.058(9.1); 8.714(6.6);8.710(7.3); 8.702(7.1); 8.698(7.3); 8.543(2.9); 8.528(6.3); 8.514(3.0);8.317(0.6); 8.237(3.6); 8.232(5.3); 8.227(3.9); 8.217(4.0); 8.212(5.8);8.207(4.1); 7.656(9.5); 7.633(3.5); 7.615(8.3); 7.609(10.3); 7.591(9.1);7.583(6.9); 7.572(9.3); 7.563(5.7); 7.552(5.8); 7.161(0.4); 7.099(0.5);7.050(16.0); 6.941(0.4); 5.757(3.2); 4.483(12.6); 4.469(12.6);3.903(1.3); 3.800(0.5); 3.327(183.9); 2.676(1.2); 2.672(1.8);2.667(1.3); 2.525(4.0); 2.511(99.6); 2.507(202.4); 2.503(270.1);2.498(201.5); 2.333(1.3); 2.329(1.8); 2.325(1.4); 1.989(0.6);0.146(1.4); 0.008(9.9); 0.000(288.4); −0.008(11.9); −0.150(1.4)

Step 2:2-(Pyridin-3-yl)-6-[3-(trifluoromethyl)benzyl][1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(28)

110 mg (0.29 mmol) of4-amino-2-(pyridin-3-yl)-N-[3-(trifluoromethyl)benzyl]-1,3-thiazole-5-carboxamide(II-28) were initially charged in N,N-dimethylacetamide. 25 mg (0.14mmol) of p-toluenesulphonic acid and 129 mg (0.87 mmol) of triethylorthoformate were added thereto and the reaction mixture was heated at130° C. in a CEM Discover microwave at 200 watts for 1 h. Saturatedsodium bicarbonate solution was added to the cooled reaction mixturewhich was then extracted repeatedly with dichloromethane. The combinedorganic phases were dried over magnesium sulfate, filtered andconcentrated. The residue was then purified by MPLC using the mobilephase cyclohexane/ethyl acetate. After evaporation of the solvent, theproduct was triturated with pentane/ethyl acetate and sonicated. Thecrystals obtained in this manner were filtered off with suction. Thisgave 38 mg (98.3% pure, 33.1% of theory) of the title compound (28).

1H-NMR (600.1 MHz, CD3CN): δ=9.2734(3.7); 9.2728(3.7); 9.270(3.8);8.751(2.8); 8.748(2.9); 8.743(2.9); 8.740(2.8); 8.469(9.8); 8.403(1.8);8.400(2.4); 8.399(2.3); 8.396(1.7); 8.389(1.9); 8.387(2.4); 8.386(2.3);8.383(1.7); 7.744(3.9); 7.662(2.1); 7.650(3.1); 7.641(2.5); 7.576(2.2);7.563(3.2); 7.550(1.3); 7.534(2.3); 7.533(2.2); 7.526(2.3); 7.525(2.2);7.521(2.3); 7.520(2.1); 7.513(2.2); 7.512(2.0); 5.293(16.0);2.957(13.9); 2.827(11.1); 2.154(11.6); 1.972(12.0); 1.967(0.5);1.959(0.6); 1.955(0.8); 1.951(5.6); 1.947(10.0); 1.943(14.5);1.938(9.7); 1.934(4.8); 0.000(6.8)

Preparation Example 7:2-(Pyridin-3-yl)-6-(pyridin-2-ylmethyl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(34) Step 1:4-Amino-2-(pyridin-3-yl)-N-(pyridin-2-ylmethyl)-1,3-thiazole-5-carboxamide(II-34)

1 g (4.0 mmol) of ethyl4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate (III-1) wereinitially charged in ethanol, and 2.25 g of potassium hydroxide (40mmol), dissolved in ethanol, were added. The reaction mixture wasstirred at 50° C. for 4 h and then concentrated to dryness. The residuewas suspended in a little water and the product was precipitated with10% strength aqueous citric acid solution. The insoluble fraction wasfiltered off with suction and dried well under reduced pressure. Theresulting 4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylic acid (583mg, 100% pure, 65.7% of theory) was directly reacted further.

LC-MS: mass found [m/z]=221.03

148 mg (0.67 mmol) of 4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylicacid and 237 mg (0.74 mmol) ofO-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate(TBTU) were initially charged in DMF, and the mixture was stirred for 10minutes. 73 mg (0.67 mmol) of 1-(pyridin-2-yl)methanamine and 130 mg (1mmol) of N,N-diisopropylethylamine, dissolved in dimethylformamide, werethen added. The reaction mixture was stirred at room temperatureovernight and then concentrated under reduced pressure. Furtherpurification of the residue was then carried out by columnchromatography using MPLC. This gave 192 mg (43.0% pure, 39.5% oftheory) of the title compound (II-34).

LC-MS: mass found [m/z]=311.08

Step 2:2-(Pyridin-3-yl)-6-(pyridin-2-ylmethyl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(34)

96 mg (0.31 mmol) of4-amino-2-(pyridin-3-yl)-N-(pyridin-2-ylmethyl)-1,3-thiazole-5-carboxamide(II-34) were initially charged in 1.1 g of N,N-dimethylacetamide. 2.4 mg(0.015 mmol) of p-toluenesulphonic acid and 69 mg (0.46 mmol) oftriethyl orthoformate were added and the reaction mixture was heated at120° C. in a CEM Discover microwave at 200 watts for 10 min. Water wasadded to the cooled reaction mixture which was then extracted repeatedlywith ethyl acetate. The combined organic phases were dried over sodiumsulphate, filtered and concentrated. Further purification of the residuewas then carried out by MPLC using the mobile phasedichloromethane/methanol (10:1) as a gradient. This gave 9.5 mg (100.0%pure, 9.6% of theory) of the title compound (34).

1H NMR (400.0 MHz, d₆-DMSO): δ=9.324 (8.2); 9.320 (8.0); 8.828 (5.9);8.819 (5.7); 8.652 (16.0); 8.533 (4.1); 8.528 (5.4); 8.523 (3.9); 8.513(4.3); 8.508 (5.6); 8.503 (3.8); 7.673 (4.7); 7.661 (4.8); 7.653 (4.6);7.641 (4.2); 6.830 (1.0); 6.818 (1.8); 6.805 (0.9); 6.700 (2.0); 6.688(3.9); 6.676 (2.0); 6.570 (1.0); 6.558 (2.0); 6.546 (1.0); 4.914 (5.2);4.875 (10.9); 4.837 (5.5); 3.905 (7.6); 3.506 (0.4); 3.338 (626.8);3.225 (1.1); 3.062 (0.9); 2.677 (2.1); 2.672 (2.7); 2.668 (2.1); 2.508(339.6); 2.503 (425.1); 2.499 (319.3); 2.334 (1.9); 2.330 (2.5); 2.325(1.9); 1.298 (0.4); 1.258 (0.5); 1.233 (0.7); 1.145 (0.7); 0.000 (37.7)

Preparation Example 8:6-[(2-Methyl-1,3-thiazol-4-yl)methyl]-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(38) Step 1:4-Amino-N-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-38)

Under argon, 0.75 ml of a 2M trimethylaluminium solution (1.5 mmol) intoluene were slowly added dropwise to 193 mg (1.5 mmol) of1-(2-methyl-1,3-thiazol-4-yl)methanamine in 12 ml of 1,2-dichloroethane,and the mixture was stirred at room temperature for 30 min 250 mg (1.0mmol) of ethyl 4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate(III-1) were then added a little at a time, and the reaction mixture wassubsequently heated under reflux overnight. After cooling, the reactionmixture was, with argon, carefully squeezed onto a 10% potassium sodiumtartrate solution (about 120 ml). The mixture was extracted three timeswith dichloromethane, and the organic phase was removed, dried oversodium sulphate, filtered and concentrated. The residue was stirred witha little n-pentane/ethyl acetate to give a suspension. The insolublefraction was filtered off with suction and then triturated withacetonitrile. The solid which had been filtered off was then dried underreduced pressure. This gave 71 mg (96.1% pure, 20.5% of theory) of thetitle compound.

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.059 (2.1); 9.054 (2.0); 8.711 (1.5);8.708 (1.6); 8.699 (1.6); 8.695 (1.6); 8.426 (0.7); 8.412 (1.4); 8.398(0.7); 8.231 (0.8); 8.226 (1.2); 8.221 (0.9); 8.211 (0.9); 8.206 (1.3);8.201 (0.9); 7.581 (1.2); 7.569 (1.2); 7.561 (1.1); 7.549 (1.1); 7.166(3.7); 7.035 (3.4); 4.433 (2.9); 4.419 (2.9); 3.904 (1.0); 3.330 (28.0);2.629 (16.0); 2.507 (25.7); 2.503 (33.6); 2.499 (25.3); 1.278 (0.5);0.008 (1.1); 0.000 (26.2); −0.008 (1.2)

Step 2:6-[(2-Methyl-1,3-thiazol-4-yl)methyl]-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(38)

55 mg (0.17 mmol) of4-amino-N-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-38) were initially charged in 0.5 ml of N,N-dimethylacetamide. 14 mg(0.08 mmol) of p-toluenesulphonic acid and 49 mg (0.33 mmol) of triethylorthoformate were added thereto and the reaction mixture was heated at130° C. in a CEM Discover microwave at 200 watts for 1 h. Water wasadded to the cooled reaction mixture which was then extracted repeatedlywith dichloromethane. The combined organic phases were washed withsaturated sodium chloride solution, dried over magnesium sulphate,filtered and concentrated. After evaporation of the solvent, the residuewas triturated with acetonitrile/ethyl acetate and the crystals obtainedin this manner were filtered off with suction. This gave 11 mg (80.0%pure, 15.5% of theory) of the title compound (38).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.305(2.2); 9.301(2.3); 8.815(1.6);8.812(1.9); 8.798(6.3); 8.511(1.3); 8.506(1.0); 8.495(1.0); 8.490(1.4);8.486(1.1); 7.661(1.3); 7.648(1.3); 7.641(1.3); 7.628(1.2); 7.454(4.1);7.277(0.5); 5.759(0.4); 5.308(7.1); 4.489(0.4); 4.476(0.4); 3.332(61.6);2.945(0.9); 2.784(0.8); 2.672(0.9); 2.655(1.3); 2.637(2.1); 2.611(16.0);2.507(95.2); 2.503(124.7); 2.499(102.9); 2.446(0.4); 2.330(0.8);2.288(0.7); 1.958(0.8); 1.313(0.5); 0.146(0.4); 0.000(71.2); −0.150(0.4)

Preparation Example 13:6-(Cyclopropylmethyl)-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(39) Step 1:4-Amino-N-(cyclopropylmethyl)-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-39)

Under argon, 1.5 ml of a 2M trimethylaluminium solution (3.01 mmol) intoluene were slowly added dropwise with ice cooling to 213 mg (3.00mmol) of 1-cyclopropylmethanamine in 15 ml of 1,2-dichloroethane, andthe mixture was stirred at room temperature for 60 min. 373 mg (1.50mmol) of ethyl 4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate(III-1) were then added, and the reaction mixture was subsequentlyheated under reflux overnight. After cooling, the reaction mixture wascarefully discharged into a 10% potassium sodium tartrate solution(about 100 ml). The mixture was extracted three times with methylenechloride, and the combined organic phases were dried over sodiumsulphate, filtered and concentrated. The residue was stirred with alittle acetonitrile to give a suspension. The insoluble portion wasfiltered off with suction and dried under reduced pressure. This gave300 mg (100% pure, 73.0% of theory) of the title compound (II-39).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.056(9.2); 9.052(9.7); 8.710(6.7);8.707(7.1); 8.699(7.2); 8.695(7.1); 8.229(3.8); 8.226(5.4); 8.220(3.9);8.210(4.1); 8.205(5.7); 8.200(4.0); 8.025(3.0); 8.012(5.9); 7.998(3.1);7.579(4.9); 7.567(5.0); 7.559(5.0); 7.547(4.6); 7.027(16.0); 3.454(4.0);3.437(9.3); 3.422(9.5); 3.404(4.3); 3.312(106.1); 2.671(1.1);2.573(1.2); 2.556(2.1); 2.545(3.8); 2.527(7.5); 2.506(132.9);2.502(168.0); 2.498(133.8); 2.470(2.8); 2.452(1.3); 2.329(1.1);0.000(11.5)

Step 2:6-(Cyclopropylmethyl)-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(39)

100 mg (0.37 mmol) of4-amino-N-(cyclopropylmethyl)-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-39) were initially charged in 1 ml of N,N-dimethylacetamide. 31 mg(0.18 mmol) of p-toluenesulphonic acid and 162 mg (1.09 mmol) oftriethyl orthoformate were added thereto and the reaction mixture washeated at 130° C. in a CEM Discover microwave at 200 watts for 1 h. Thecooled reaction mixture was concentrated under reduced pressure and theresidue was purified chromatographically by MPLC. This gave, in total, 2mg (100% pure, 2.2% of theory) of the title compound (39).

1H-NMR (601.6 MHz, CDCl₃): δ=9.341(5.1); 9.338(5.0); 8.781(3.5);8.775(3.6); 8.426(2.9); 8.423(3.9); 8.420(2.8); 8.413(3.1); 8.410(4.0);8.407(2.8); 8.299(16.0); 7.484(3.2); 7.476(3.3); 7.471(3.3); 7.463(3.1);7.432(0.6); 7.261(86.9); 7.084(0.5); 5.299(2.5); 3.958(15.5);3.946(15.6); 3.278(0.4); 3.269(0.5); 3.266(0.4); 3.257(0.4); 2.232(0.4);2.220(0.6); 2.207(0.4); 1.637(0.4); 1.558(13.5); 1.445(0.4); 1.368(0.5);1.360(0.9); 1.355(1.3); 1.352(0.9); 1.347(2.2); 1.342(2.1); 1.339(1.8);1.334(3.5); 1.329(2.0); 1.326(2.4); 1.321(2.7); 1.313(2.0); 1.309(1.8);1.301(1.4); 1.255(7.8); 0.892(1.0); 0.881(1.8); 0.869(1.1); 0.856(0.4);0.841(0.4); 0.715(2.2); 0.707(6.7); 0.705(7.1); 0.697(3.5); 0.694(7.0);0.692(6.7); 0.684(2.5); 0.577(0.4); 0.575(0.4); 0.564(0.4); 0.562(0.4);0.491(2.4); 0.483(8.8); 0.473(8.4); 0.465(2.0); 0.276(0.4); 0.267(0.5);0.097(0.4); 0.005(2.9); 0.000(86.6); −0.006(3.2); −0.100(0.4)

Preparation Example 14:N,N-Dimethyl-3-[7-oxo-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-6(7H)-yl]benzenesulphonamide(42) Step 1:4-Amino-N-[3-(dimethylsulphamoyl)phenyl]-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-42)

Under argon, 9.0 ml of a 2M trimethylaluminium solution (18.1 mmol) intoluene were slowly added dropwise with ice cooling to 3.6 g (18.1 mmol)of 3-amino-N,N-dimethylbenzenesulphonamide in 200 ml of1,2-dichloroethane, and the mixture was stirred at room temperature for60 min 1.5 g (6.02 mmol) of ethyl4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate (III-1) were thenadded, and the reaction mixture was subsequently heated under refluxovernight. After cooling, the reaction mixture was carefully dischargedinto a 10% potassium sodium tartrate solution (about 250 ml). Themixture was extracted three times with methylene chloride, and thecombined organic phases were dried over sodium sulphate, filtered andconcentrated. The residue was stirred with a little acetonitrile to givea suspension. The insoluble portion was washed with n-pentane, filteredoff with suction and dried under reduced pressure. The solid was thenpurified by MPLC using the mobile phase cyclohexane/ethyl acetate. Thisgave 340 mg (100% pure, 14.0% of theory) of the title compound (II-42).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.997(1.7); 9.107(1.2); 9.102(1.3);8.745(0.8); 8.742(0.9); 8.734(0.9); 8.731(0.9); 8.279(0.4); 8.275(0.7);8.271(0.5); 8.259(0.5); 8.255(0.8); 8.251(0.5); 8.169(1.5); 8.062(0.6);8.040(0.7); 7.614(1.2); 7.603(0.7); 7.594(1.8); 7.583(0.7); 7.574(0.8);7.424(0.9); 7.404(0.7); 7.322(1.9); 3.320(8.0); 2.638(16.0);2.507(14.9); 2.503(19.6); 2.499(15.3); 1.989(0.9); 1.176(0.5);0.000(0.4)

Step 2:N,N-Dimethyl-3-[7-oxo-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-6(7H)-yl]benzenesulphonamide(42)

320 mg (0.79 mmol) of4-amino-N-[3-(dimethylsulphamoyl)phenyl]-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-42) were initially charged in N,N-dimethylacetamide. 68 mg (0.40mmol) of p-toluenesulphonic acid and 260 mg (1.75 mmol) of triethylorthoformate were added thereto and the reaction mixture was heated at130° C. in a CEM Discover microwave at 200 watts for 1 h. The cooledreaction mixture was concentrated under reduced pressure, and theresidue was triturated with acetonitrile and the product was filteredoff as a solid. The solid was then dried by pressing it onto a clayplate and purified by MPLC using the mobile phase n-hexane/ethylacetate. This gave 320 mg (100% pure, 97.6% of theory) of the titlecompound (42).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.350(1.3); 9.345(1.3); 8.835(0.9);8.831(1.0); 8.823(1.0); 8.819(1.0); 8.714(3.3); 8.560(0.5); 8.556(0.7);8.551(0.5); 8.540(0.6); 8.535(0.8); 8.531(0.5); 8.055(1.6); 7.967(0.6);7.962(0.4); 7.948(1.0); 7.944(0.7); 7.929(0.5); 7.925(0.4); 7.909(1.4);7.894(1.3); 7.875(1.1); 7.856(0.4); 7.680(0.7); 7.668(0.7); 7.660(0.7);7.648(0.7); 3.320(7.9); 2.681(16.0); 2.507(13.0); 2.502(16.4);2.498(12.5); 0.000(16.1)

Preparation Example 15:6-{2,4-Dimethyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(50) Step 1:4-Amino-N-{2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-49)

Under argon, 1.5 ml of a 2M trimethylaluminium solution (3.01 mmol) intoluene were slowly added dropwise with ice cooling to 708 mg (3.01mmol) of 2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulphanyl]aniline in1,2-dichloroethane, and the mixture was stirred at room temperature for30 min 250 mg (1.00 mmol) of ethyl4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate (III-1) were thenadded, and the reaction mixture was subsequently heated under refluxovernight. After cooling, the reaction mixture was carefully dischargedinto a 10% potassium sodium tartrate solution (about 120 ml). Themixture was extracted three times with methylene chloride, and thecombined organic phases were dried over sodium sulphate, filtered andconcentrated. The residue was stirred with a little acetonitrile to givea suspension. The insoluble portion was filtered off with suction anddried under reduced pressure. This gave 158 mg (100% pure, 35.9% oftheory) of the title compound (II-49).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.328(4.1); 9.086(3.2); 9.081(3.1);8.729(2.3); 8.726(2.4); 8.717(2.4); 8.714(2.4); 8.259(1.3); 8.254(1.8);8.249(1.3); 8.239(1.4); 8.234(1.9); 8.229(1.3); 7.598(1.7); 7.586(1.7);7.579(1.7); 7.566(1.6); 7.468(5.9); 7.174(5.0); 7.133(5.2); 3.878(1.2);3.852(3.8); 3.826(4.0); 3.800(1.4); 3.330(19.9); 2.507(38.9);2.503(48.8); 2.499(36.6); 2.365(14.9); 2.330(0.4); 2.325(0.3);2.163(16.0); 0.000(40.2)

Step 2:6-{2,4-Dimethyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(49)

600 mg (1.37 mmol) of4-amino-N-{2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(11-49) were initially charged in 15 ml (90.2 mmol) of triethylorthoformate. 118 mg (0.68 mmol) of p-toluenesulphonic acid were addedand the reaction mixture was heated at 170° C. in a CEM Discovermicrowave for 2 h. The cooled reaction mixture was concentrated underreduced pressure and purified chromatographically by MPLC using themobile phase cyclohexane/ethyl acetate. This gave, in total, 200 mg(95.3% pure, 31.1% of theory) of the title compound (49).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.347(2.9); 9.342(3.0); 8.838(2.3);8.834(2.4); 8.826(2.4); 8.822(2.5); 8.558(1.3); 8.554(1.9); 8.548(1.4);536(10.2); 8.528(1.5); 8.317(0.8); 7.924(0.4); 7.683(1.9); 7.675(6.4);7.665(2.0); 7.651(1.5); 7.360(4.7); 6.025(1.0); 4.055(0.6); 4.038(2.6);4.020(2.4); 4.014(3.6); 4.002(0.9); 3.988(3.6); 3.962(1.3); 3.855(0.8);3.837(0.8); 3.392(0.3); 3.374(0.5); 3.332(421.8); 2.676(1.7);2.671(2.3); 2.667(1.7); 2.525(5.6); 2.511(131.6); 2.507(269.9);2.502(357.0); 2.498(264.5); 2.494(133.5); 2.407(15.0); 2.365(0.4);2.334(1.8); 2.329(2.4); 2.325(1.8); 2.078(16.0); 1.989(7.6); 1.890(0.3);1.398(1.9); 1.235(0.6); 1.193(2.1); 1.175(4.1); 1.157(2.1); 1.100(0.8);1.083(1.5); 1.065(0.8); 0.146(0.5); 0.008(3.7); 0.000(116.2);−0.008(4.9); −0.150(0.5)

Step 3:6-{2,4-Dimethyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(50)

At 0° C., 127 mg (77% strength, 0.57 mmol) of meta-chloroperbenzoic acidwere added to a solution of 250.0 mg (0.56 mmol) of6-{2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(49) in 10 ml of dichloromethane. The reaction mixture was stirred atroom temperature for 1 hour, and aqueous sodium bisulphite solution wasthen added. The organic phase was separated off and then washed withsaturated sodium carbonate solution and dried over sodium sulphate.After evaporation of the solvent, the residue was purifiedchromatographically by MPLC using the mobile phase cyclohexane/ethylacetate. This gave 154 mg (99.0% pure, 58.88% of theory) of the titlecompound (50).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.351(4.6); 9.346(4.6); 8.839(3.4);8.835(3.7); 8.827(3.6); 8.823(3.7); 8.591(14.3); 8.561(1.9); 8.556(2.7);8.551(1.9); 8.541(2.0); 8.536(2.8); 8.531(1.9); 8.317(1.3); 7.937(6.3);7.928(4.2); 7.685(2.6); 7.673(2.6); 7.667(2.5); 7.653(2.4); 7.496(3.0);7.470(4.4); 4.323(0.5); 4.295(0.6); 4.286(0.7); 4.259(0.7); 4.178(0.6);4.171(0.6); 4.151(1.8); 4.144(1.8); 4.124(1.8); 4.117(1.8); 4.097(0.7);4.090(0.6); 4.055(0.4); 4.037(1.0); 4.020(1.0); 4.002(0.4); 3.977(0.7);3.951(0.8); 3.940(0.7); 3.924(0.3); 3.914(0.7); 3.372(0.9);3.332(833.0); 2.676(2.9); 2.671(3.9); 2.667(2.9); 2.525(9.7);2.507(449.3); 2.502(587.2); 2.498(437.0); 2.451(12.1); 2.446(16.0);2.408(0.8); 2.353(0.6); 2.334(3.2); 2.329(4.0); 2.325(3.0); 2.279(0.4);2.258(0.5); 2.188(15.9); 2.182(12.0); 1.989(4.2); 1.193(1.1);1.175(2.3); 1.157(1.1); 0.146(0.8); 0.008(6.5); 0.000(190.8);−0.008(8.2); −0.150(0.9)

Preparation Example 16:2-({4-Fluoro-2-methyl-5-[7-oxo-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-6(7H)-yl]phenyl}sulphinyl)-N,N-dimethylacetamide(55) Step 1:2-[(5-Amino-4-fluoro-2-methylphenyl)sulphanyl]-N,N-dimethylacetamide

100 ml of dry acetone were added to 1.50 g (9.54 mmol) of5-amino-4-fluoro-2-methylbenzenethiol, 1.28 g (10.50 mmol) of2-chloro-N,N-dimethylacetamide and 6.22 g (19.08 mmol) of caesiumcarbonate, and the mixture was stirred under reflux overnight. Thecooled reaction mixture was added to a mixture of ethyl acetate andsodium carbonate and the organic phase was separated off. The aqueousphase was subsequently extracted repeatedly with ethyl acetate, and thecombined organic phases were dried over magnesium sulfate, filtered andconcentrated. This gave 2.10 mg (90.0% pure, 81.75% of theory) of thetitle compound2-[(5-amino-4-fluoro-2-methylphenypsulphanyl]-N,N-dimethylacetamide.

1H-NMR (601.6 MHz, CDCl₃): δ=7.264(2.5); 6.995(2.3); 6.980(2.3);6.836(1.7); 6.816(1.7); 4.079(0.4); 3.605(10.1); 3.098(0.6); 3.034(0.4);3.025(16.0); 2.991(0.6); 2.968(0.4); 2.951(14.4); 2.313(13.0);2.170(1.4); 0.000(2.4)

Step 2:4-Amino-N-(5-{[2-(dimethylamino)-2-oxoethyl]sulphanyl}-2-fluoro-4-methylphenyl)-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-54)

Under argon, 3.94 ml of a 2M trimethylaluminium solution (7.88 mmol) intoluene were slowly added dropwise with ice cooling to 2.10 g (7.88mmol) of2-[(5-amino-4-fluoro-2-methylphenyl)sulphanyl]-N,N-dimethylacetamide(see Preparation Example 16, Step 1) in 150 ml of 1,2-dichloroethane,and the mixture was stirred at room temperature for 60 min 655 mg (2.63mmol) of ethyl 4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate(III-1) were then added, and the reaction mixture was subsequentlyheated under reflux overnight. After cooling, the reaction mixture wascarefully discharged into a 10% potassium sodium tartrate solution(about 200 ml). The mixture was extracted three times with methylenechloride, and the combined organic phases were dried over magnesiumsulphate, filtered and concentrated. The residue was then purifiedchromatographically by MPLC using the mobile phase cyclohexane/ethylacetate. This gave 370 mg (47.0% pure, 14.86% of theory) of the titlecompound (II-54) which was directly reacted further in Step 3 withoutfurther purification.

HPLC-MS (ESI positive, m/z): [M+H]=446.0

Step 3:2-({4-Fluoro-2-methyl-5-[7-oxo-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-6(7H)-yl]phenyl}sulphanyl)-N,N-dimethylacetamide(54)

370 mg (47% pure, 0.39 mmol) of4-amino-N-(5-{[2-(dimethylamino)-2-oxoethyl]sulphanyl}-2-fluoro-4-methylphenyl)-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-54) were initially charged in 1 ml of N,N-dimethylacetamide. 34 mg(0.20 mmol) of p-toluenesulphonic acid and 174 mg (1.17 mmol) oftriethyl orthoformate were added thereto and the reaction mixture washeated at 130° C. in a CEM Discover microwave at 200 watts for 1 h. Thecooled reaction mixture was concentrated under reduced pressure, and theresidue was triturated with acetonitrile and the product was filteredoff as a solid. The solid was then dried by pressing it onto a clayplate and purified by MPLC using the mobile phase acetonitrile/water.This gave 170 mg (100% pure, 95.61% of theory) of the title compound(54).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.347(2.8); 9.342(2.6); 8.837(2.0);8.825(2.0); 8.668(5.5); 8.552(1.6); 8.532(1.6); 8.141(0.9); 7.718(2.4);7.700(2.4); 7.682(1.5); 7.669(1.5); 7.662(1.4); 7.649(1.3); 7.448(2.1);7.422(2.1); 5.754(0.6); 4.011(8.8); 3.320(45.4); 3.027(16.0);2.891(0.5); 2.832(14.9); 2.731(0.5); 2.670(0.6); 2.502(95.0);2.406(12.3); 2.328(0.6); 0.000(4.0)

Step 4:2-({4-Fluoro-2-methyl-5-[7-oxo-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-6(7H)-yl]phenyl}sulphinyl)-N,N-dimethylacetamide(55)

At 0° C., 81 mg (77% strength, 0.36 mmol) of meta-chloroperbenzoic acidwere added to a solution of 170 mg (0.36 mmol) of2-({4-fluoro-2-methyl-5-[7-oxo-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-6(7H)-yl]phenyl}sulphanyl)-N,N-dimethylacetamide(54) in 1 ml of dichloromethane. The reaction mixture was stirred atroom temperature for 1 hour, and aqueous sodium carbonate solution wasthen added. The aqueous phase was separated off and extracted repeatedlywith dichloromethane, and the combined organic phases were dried,filtered and concentrated. The residue was then purifiedchromatographically by MPLC using the mobile phase cyclohexane/ethylacetate. This gave 119 mg (100% pure, 71.2% of theory) of the titlecompound (55).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.350(3.2); 9.345(3.1); 8.838(2.2);8.835(2.3); 8.826(2.3); 8.823(2.3); 8.722(6.2); 8.556(1.8); 8.540(1.4);8.535(1.9); 8.531(1.3); 8.139(4.6); 8.119(2.9); 7.685(1.7); 7.672(1.7);7.665(1.7); 7.653(1.5); 7.568(2.4); 7.541(2.4); 4.185(1.3); 4.148(2.5);4.086(1.2); 4.047(0.6); 3.340(160.4); 2.955(16.0); 2.863(15.8);2.672(0.6); 2.507(78.3); 2.503(97.2); 2.473(15.1); 2.330(0.6);0.000(3.2)

Preparation Example 17:6-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-5-methyl-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(57) Step 1:6-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-5-methyl-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(56)

200 mg (0.45 mmol) of4-amino-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-21) were initially charged in 1 ml of N,N-dimethylacetamide. 39 mg(0.23 mmol) of p-toluenesulphonic acid and 220 mg (1.36 mmol) oftriethyl orthoacetate were added and the reaction mixture was heated at130° C. in a CEM Discover microwave at 200 watts for 30 min. The cooledreaction mixture was concentrated under high vacuum. The residue wasthen purified by MPLC using the mobile phase acetonitrile/water. Thisgave 30 mg (100% pure, 14.2% of theory) of the title compound (56).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.333(2.4); 9.328(2.4); 8.834(1.8);8.830(2.0); 8.822(1.9); 8.818(2.0); 8.535(1.1); 8.531(1.4); 8.526(1.1);8.515(1.2); 8.510(1.5); 8.506(1.1); 7.939(2.4); 7.920(2.4); 7.680(1.4);7.668(1.4); 7.661(1.4); 7.648(1.3); 7.541(2.1); 7.515(2.1); 4.085(0.5);4.071(0.5); 4.060(0.6); 4.046(1.3); 4.037(0.6); 4.021(1.3); 4.012(1.3);3.995(0.7); 3.986(1.3); 3.972(0.5); 3.960(0.5); 3.946(0.5); 3.329(49.4);2.676(0.4); 2.672(0.5); 2.668(0.4); 2.525(1.3); 2.512(29.6);2.507(59.8); 2.503(79.0); 2.498(58.4); 2.494(29.1); 2.469(13.3);2.443(0.6); 2.417(0.6); 2.339(0.3); 2.334(0.5); 2.329(0.6); 2.325(0.5);2.302(0.4); 2.281(16.0); 2.076(1.0); 0.008(1.9); 0.000(57.6);−0.009(2.3)

Step 2:6-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-5-methyl-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(57)

At 0° C., 12 mg (77% strength, 0.06 mmol) of meta-chloroperbenzoic acidwere added to a solution of 25 mg (0.06 mmol) of6-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-5-methyl-2-(pyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(56) in 1 ml of dichloromethane. The reaction mixture was stirred atroom temperature for 1 hour, and aqueous sodium carbonate solution wasthen added. The aqueous phase was separated off and extracted repeatedlywith dichloromethane, and the combined organic phases were dried,filtered and concentrated. This gave 14 mg (88.0% pure, 47.7% of theory)of the title compound (57).

1H-NMR (601.6 MHz, CDCl₃): δ=9.363(2.0); 8.807(1.5); 8.469(0.8);8.466(1.1); 8.463(0.8); 8.452(1.9); 8.441(0.9); 8.438(1.1); 8.435(0.8);8.065(1.7); 8.029(1.8); 8.017(1.8); 8.003(1.8); 7.991(1.8); 7.979(1.0);7.966(1.1); 7.556(0.7); 7.554(0.7); 7.542(0.9); 7.541(0.9); 7.526(0.9);7.519(1.3); 7.513(1.7); 7.507(1.3); 7.500(0.9); 7.415(1.0); 7.402(1.7);7.389(0.8); 7.304(1.8); 7.302(1.9); 7.288(1.9); 7.286(1.8); 7.272(7.2);5.302(6.3); 3.617(0.5); 3.609(0.4); 3.601(0.6); 3.593(1.0); 3.576(1.1);3.563(1.1); 3.555(0.3); 3.547(3.0); 3.539(0.6); 3.530(3.1); 3.523(0.8);3.514(1.2); 3.506(0.7); 2.590(0.5); 2.517(16.0); 2.501(0.6); 2.493(0.4);2.484(0.3); 2.418(0.7); 2.408(12.8); 2.395(0.6); 2.386(12.7);2.378(1.1); 2.369(0.4); 2.356(0.5); 2.352(0.4); 2.344(0.4); 2.332(0.4);1.335(0.5); 1.329(0.3); 1.306(0.6); 1.295(0.9); 1.286(1.3); 1.283(1.3);1.271(1.3); 1.255(6.2); 1.232(0.7); 1.221(0.5); 1.212(0.5); 0.891(0.8);0.880(1.4); 0.868(1.0); 0.856(0.5); 0.843(0.9); 0.841(0.9); 0.834(0.9);0.005(0.5); 0.000(14.7); −0.006(0.7)

Preparation Example 18:3-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-6-(pyridin-3-yl)[1,3]thiazolo[4,5-d][1,2,3]triazin-4(3H)-one(59) Step 2:3-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-6-(pyridin-3-yl)[1,3]thiazolo[4,5-d][1,2,3]triazin-4(3H)-one(58)

160 mg (0.36 mmol) of4-amino-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyridin-3-yl)-1,3-thiazole-5-carboxamide(II-21) were initially charged in 4 ml of concentrated hydrochloricacid. 212 mg (3.07 mmol) of sodium nitrite, dissolved in 4 ml of water,were then added dropwise to this mixture, and the mixture was stirred at70° C. for 4 h. The cooled mixture was then added to saturated sodiumcarbonate solution and extracted repeatedly with dichloromethane. Thecombined organic phases were dried over magnesium sulphate, filtered andconcentrated. This gave 112 mg (90.0% pure, 61.5% of theory) of thetitle compound (58).

1H-NMR (400.0 MHz, DMSO): δ=9.430(10.3); 9.425(10.4); 8.891(8.1);8.887(8.8); 8.879(8.5); 8.875(8.7); 8.651(4.7); 8.646(6.4); 8.641(4.7);8.631(5.1); 8.625(6.5); 8.621(4.7); 8.317(0.4); 8.260(1.0); 8.242(1.1);7.992(9.9); 7.973(9.9); 7.729(6.1); 7.717(6.0); 7.709(6.0); 7.697(6.2);7.673(0.9); 7.583(8.6); 7.556(8.5); 5.758(16.0); 4.361(0.7); 4.351(0.4);4.344(0.4); 4.324(0.4); 4.086(0.4); 4.059(0.4); 4.049(0.4); 4.018(4.1);3.993(12.7); 3.967(13.1); 3.941(4.5); 3.331(218.6); 2.677(1.1);2.672(1.5); 2.668(1.1); 2.512(92.5); 2.508(154.3); 2.503(197.3);2.499(145.6); 2.495(73.3); 2.374(0.4); 2.353(0.4); 2.334(1.0);2.330(1.3); 2.326(1.0); 1.343(0.4); 1.326(0.8); 1.308(0.4); 0.146(0.4);0.008(3.0); 0.000(84.9); −0.008(3.4); −0.150(0.4)

Step 2:3-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-6-(pyridin-3-yl)[1,3]thiazolo[4,5-d][1,2,3]triazin-4(3H)-one(59)

At 0° C., 44 mg (77% strength, 0.19 mmol) of meta-chloroperbenzoic acidwere added to a solution of 96 mg (90% pure, 0.19 mmol) of3-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-6-(pyridin-3-yl)[1,3]thiazolo[4,5-d][1,2,3]triazin-4(3H)-one(58) in 1 ml of dichloromethane. The reaction mixture was stirred atroom temperature for 40 minutes, and aqueous sodium carbonate solutionwas then added. The aqueous phase was separated off and extractedrepeatedly with dichloromethane, and the combined organic phases weredried, filtered and concentrated. The residue was then purified by MPLCusing the mobile phase acetonitrile/water. This gave 30 mg (100% pure,33.5% of theory) of the title compound (59).

1H-NMR (400.0 MHz, DMSO): δ=9.432(5.9); 9.428(6.0); 8.891(4.5);8.887(4.8); 8.879(4.8); 8.875(4.8); 8.652(2.6); 8.648(3.5); 8.642(2.6);8.632(2.8); 8.626(3.7); 8.622(2.7); 8.260(5.9); 8.241(6.0); 7.729(3.3);7.717(3.3); 7.709(3.5); 7.699(7.6); 7.673(4.8); 5.758(16.0); 4.415(0.5);4.388(1.7); 4.378(0.8); 4.360(2.0); 4.351(2.3); 4.333(0.8); 4.323(2.3);4.296(0.7); 4.112(0.6); 4.085(2.0); 4.075(0.7); 4.058(2.3); 4.048(1.9);4.031(0.9); 4.021(1.8); 3.994(0.6); 3.331(101.6); 2.676(0.7);2.672(1.0); 2.668(0.8); 2.507(117.2); 2.503(134.4); 2.498(99.6);2.334(0.6); 2.330(0.9); 2.325(0.7); 1.233(0.7); 0.008(1.1); 0.000(27.5)

Preparation Example 19:2-(Pyridin-3-yl)-6-{4-[(trifluoromethyl)sulphinyl]phenyl}[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(63) Step 1:4-Amino-2-(pyridin-3-yl)-N-{4-[(trifluoromethyl)sulphanyl]phenyl}-1,3-thiazole-5-carboxamide(II-62)

Under argon, 3.0 ml of a 2M trimethylaluminium solution (6.0 mmol) intoluene were slowly added dropwise with ice cooling to 1.16 g (6.0 mmol)of 4-[(trifluoromethyl)sulphanyl]aniline in 50 ml of 1,2-dichloroethane,and the mixture was stirred at room temperature for 1 hour. 500 mg (2.0mmol) of ethyl 4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate(III-1) were then added, and the reaction mixture was subsequentlyheated under reflux overnight. After cooling, the reaction mixture wascarefully discharged into a 10% potassium sodium tartrate solution(about 120 ml). The mixture was extracted three times with methylenechloride, and the combined organic phases were dried over magnesiumsulphate, filtered and concentrated. The residue was stirred with alittle acetonitrile to give a suspension. The insoluble fraction wasfiltered off with suction and then purified by MPLC using the mobilephase acetonitrile/water. This gave 130 mg (99.0% pure, 16.2% of theory)of the title compound (II-62).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.958(9.7); 9.780(0.6); 9.109(7.3);9.104(7.2); 9.103(7.2); 9.096(0.8); 8.746(5.4); 8.742(6.0); 8.734(6.2);8.730(6.1); 8.283(3.0); 8.278(4.1); 8.273(3.4); 8.263(3.6); 8.257(4.6);8.253(3.5); 7.889(1.4); 7.883(12.5); 7.878(4.6); 7.866(4.6);7.861(16.0); 7.854(2.0); 7.730(0.9); 7.725(0.3); 7.713(0.3); 7.707(1.1);7.679(12.9); 7.657(10.8); 7.615(3.8); 7.613(4.1); 7.601(4.0);7.595(3.9); 7.593(4.0); 7.583(3.6); 7.581(3.9); 7.384(1.2); 7.379(0.5);7.361(1.4); 7.337(10.7); 7.267(0.8); 3.329(92.9); 2.677(0.8);2.672(1.1); 2.668(0.8); 2.525(2.6); 2.512(58.6); 2.508(119.3);2.503(158.4); 2.499(116.9); 2.494(58.1); 2.334(0.7); 2.330(1.0);2.325(0.8); 2.321(0.4); 2.076(1.4); 0.146 (0.6); 0.008(4.8);0.000(137.9); −0.009(5.2); −0.150(0.6)

Step 2:2-(Pyridin-3-yl)-6-{4-[(trifluoromethyl)sulphanyl]phenyl}[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(62)

65 mg (0.16 mmol) of4-amino-2-(pyridin-3-yl)-N-{4-[(trifluoromethyl)sulphanyl]phenyl}-1,3-thiazole-5-carboxamide(II-62) were initially charged in 5 ml of absolute ethanol 14 mg (0.08mmol) of p-toluenesulphonic acid and 72 mg (0.49 mmol) of triethylorthoformate were added and the reaction mixture was heated at 80° C. ina CEM Discover microwave for 15 min. The reaction mixture was cooled,concentrated under reduced pressure and taken up in 3 ml ofdichloromethane. The solution was washed with 2 ml of saturated sodiumcarbonate solution and the organic phase was separated off, filtered anddried. The residue was then purified chromatographically by MPLC. Thisgave, in total, 20 mg (86.0% pure, 26.1% of theory) of the titlecompound (62).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.954(1.2); 9.347(5.1); 9.343(5.1);9.341(5.2); 9.106(0.9); 9.100(0.9); 8.835(3.9); 8.831(4.4); 8.823(4.0);8.819(4.4); 8.744(0.7); 8.740(0.8); 8.732(0.8); 8.728(0.8); 8.701(16.0);8.636(1.4); 8.558(2.1); 8.552(3.1); 8.548(2.5); 8.538(2.3); 8.532(3.3);8.528(2.5); 8.280(0.4); 8.275(0.5); 8.271(0.4); 8.260(0.4); 8.255(0.6);8.251(0.4); 7.969(7.3); 7.948(9.3); 7.881(1.5); 7.859(2.0); 7.806(1.5);7.799(11.4); 7.795(3.7); 7.783(3.0); 7.778(9.2); 7.772(1.0); 7.688(0.6);7.679(4.0); 7.667(4.3); 7.660(3.6); 7.647(4.4); 7.625(0.4); 7.612(0.5);7.600(0.5); 7.592(0.5); 7.579(0.5); 7.333(1.3); 3.324(74.8); 2.676(0.7);2.671(0.9); 2.667(0.7); 2.524(2.5); 2.511(45.7); 2.507(92.5);2.502(124.5); 2.498(94.2); 2.493(47.7); 2.333(0.5); 2.329(0.8);2.325(0.6); 1.298(0.5); 1.259(0.7); 1.233(1.0); 0.000(1.1)

Step 3:2-(Pyridin-3-yl)-6-{4-[(trifluoromethyl)sulphinyl]phenyl}[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(63)

At 0° C., 20 mg (77% strength, 0.09 mmol) of meta-chloroperbenzoic acidwere added to a solution of 35.0 mg (0.09 mmol) of2-(pyridin-3-yl)-6-{4-[(trifluoromethyl)sulphanyl]phenyl}[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(62) in 1 ml of dichloromethane. The reaction mixture was stirred atroom temperature for 90 minutes, and saturated sodium carbonate solutionwas then added. The aqueous phase was extracted three times withdichloromethane, and the combined organic phases were dried andfiltered. After evaporation of the solvent, the residue was thenpurified chromatographically using the mobile phasedichloromethane/methanol (30:1). This gave 10 mg (95.0% pure, 26.1% oftheory) of the title compound (63).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.344(0.4); 8.925(9.0); 8.748(0.7);8.714(16.0); 8.649(1.1); 8.542(0.3); 8.462(5.6); 8.446(5.9); 8.317(1.5);8.137(0.4); 8.117(0.7); 8.081(5.4); 8.061(5.8); 7.970(10.5);7.950(13.1); 7.793(14.1); 7.772(11.5); 7.689(0.8); 7.666(5.7);7.647(6.7); 7.629(4.4); 5.757(7.6); 3.507(0.3); 3.487(0.3); 3.447(0.4);3.439(0.4); 3.409(0.5); 3.326(536.7); 3.245(0.3); 2.840(0.4);2.820(0.4); 2.805(0.4); 2.765(0.4); 2.671(8.5); 2.622(1.1); 2.618(1.1);2.502(1215.9); 2.329(7.9); 2.184(0.3); 1.355(0.6); 1.299(1.8);1.259(2.9); 1.235(7.6); 1.166(0.5); 1.149(1.1); 1.066(0.4); 0.854(1.6);0.843(1.0); 0.834(1.1); 0.814(0.7); 0.784(0.5); 0.146(5.7); 0.083(0.5);0.000(1101.9); −0.150(5.9)

Preparation Example 20:2-(Pyridin-3-yl)-6-{2-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(69) Step 1:4-Amino-2-(pyridin-3-yl)-N-{2-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-1,3-thiazole-5-carboxamide(II-68)

Under argon, 3.6 ml of a 2M trimethylaluminium solution (7.22 mmol) intoluene were slowly added dropwise with ice cooling to 1.50 g (7.22mmol) of 2-[(2,2,2-trifluoroethyl)sulphinyl]aniline in 50 ml of1,2-dichloroethane, and the mixture was stirred at room temperature for1 hour. 600 mg (2.41 mmol) of ethyl4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate (III-1) were thenadded, and the reaction mixture was subsequently heated under refluxovernight. After cooling, the reaction mixture was carefully dischargedinto a 10% potassium sodium tartrate solution (about 120 ml). Themixture was extracted three times with methylene chloride, and thecombined organic phases were dried over magnesium sulphate, filtered andconcentrated. The residue was stirred with a little acetonitrile to givea suspension. The insoluble fraction was filtered off with suction andthen purified by MPLC using the mobile phase acetonitrile/water. Thisgave 240 mg (96.0% pure, 23.3% of theory) of the title compound (II-68).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.458(10.4); 9.104(6.7); 9.099(6.7);8.738(5.3); 8.734(5.7); 8.726(5.8); 8.722(5.6); 8.316(0.4); 8.279(3.0);8.275(4.2); 8.269(3.1); 8.259(3.3); 8.254(4.3); 8.249(3.1); 7.661(4.8);7.644(5.2); 7.641(5.2); 7.605(3.9); 7.603(3.9); 7.593(3.9); 7.591(3.9);7.585(3.9); 7.583(3.8); 7.573(3.7); 7.571(3.6); 7.536(4.8); 7.519(5.5);7.517(5.7); 7.365(2.4); 7.362(2.5); 7.346(5.0); 7.343(5.0); 7.327(3.3);7.324(3.1); 7.287(3.6); 7.283(3.6); 7.267(4.9); 7.264(4.9); 7.249(2.2);7.245(2.1); 7.176(12.1); 4.253(0.6); 4.235(0.6); 3.944(2.8); 3.918(8.8);3.892(9.1); 3.866(3.1); 3.330(242.9); 2.676(0.9); 2.672(1.2);2.667(0.9); 2.525(2.8); 2.507(127.7); 2.503(166.7); 2.498(124.1);2.334(0.9); 2.329(1.2); 2.325(0.9); 2.075(16.0); 1.295(0.6); 1.278(1.3);1.260(0.6); 1.233(0.7); 0.008(0.4); 0.000(10.3); −0.008(0.4)

Step 2:2-(Pyridin-3-yl)-6-{2-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(68)

5 ml (30.1 mmol) of triethyl orthoformate were added to 225 mg (0.53mmol) of4-amino-2-(pyridin-3-yl)-N-{2-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-1,3-thiazole-5-carboxamide(II-68) and 45 mg (0.26 mmol) of p-toluenesulphonic acid and thereaction mixture was heated at 170° C. in a CEM Discover microwave for60 min. The cooled reaction mixture was concentrated under reducedpressure and purified chromatographically by MPLC using the mobile phasecyclohexane/ethyl acetate. This gave, in total, 95 mg (99.0% pure, 42.5%of theory) of the title compound (68).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.348(4.6); 9.344(4.6); 8.841(3.7);8.837(4.0); 8.829(4.0); 8.825(4.0); 8.558(2.5); 8.551(16.0); 8.539(2.6);8.533(3.3); 8.529(2.4); 7.918(3.2); 7.915(3.1); 7.899(4.0); 7.688(2.9);7.686(2.8); 7.676(2.9); 7.674(2.9); 7.667(5.2); 7.663(4.0); 7.654(4.6);7.648(3.9); 7.645(5.9); 7.639(5.5); 7.635(3.0); 7.620(3.2); 7.616(2.2);7.598(3.4); 7.595(3.5); 7.579(3.1); 7.576(3.5); 7.561(1.3); 7.557(1.2);5.757(3.6); 4.056(0.6); 4.038(1.0); 4.031(1.1); 4.020(1.3); 4.017(1.0);4.006(1.3); 3.992(2.6); 3.980(0.7); 3.967(3.0); 3.944(2.9); 3.930(0.6);3.918(2.8); 3.905(1.2); 3.892(1.0); 3.878(1.2); 3.852(0.4); 3.329(31.2);2.677(0.4); 2.672(0.5); 2.668(0.4); 2.526(1.3); 2.512(26.5);2.508(53.3); 2.503(70.5); 2.499(52.7); 2.495(27.0); 2.335(0.3);2.330(0.5); 2.325(0.4); 1.990(3.7); 1.397(1.3); 1.299(0.8); 1.259(1.1);1.250(0.4); 1.234(1.6); 1.193(1.2); 1.176(2.1); 1.158(1.1); 0.146(0.6);0.008(4.9); 0.000(120.6); −0.008(6.0); −0.150(0.6)

Step 3:2-(Pyridin-3-yl)-6-{2-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(69)

At 0° C., 42 mg (77% strength, 0.19 mmol) of meta-chloroperbenzoic acidwere added to a solution of 80.0 mg (0.18 mmol) of2-(pyridin-3-yl)-6-{2-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(68) in 1 ml of dichloromethane. The reaction mixture was stirred atroom temperature for 30 minutes, and saturated sodium carbonate solutionwas then added. The aqueous phase was extracted three times withdichloromethane, and the combined organic phases were dried andfiltered. After evaporation of the solvent, the residue was thenpurified chromatographically by MPLC using the mobile phasecyclohexane/ethyl acetate. This gave 10 mg (90.0% pure, 11.3% of theory)of the title compound (69).

1H-NMR (601.6 MHz, CDCl₃): δ=9.372(12.3); 8.822(9.3); 8.817(9.2);8.465(7.5); 8.453(8.0); 8.307(16.0); 8.291(8.4); 8.278(8.2); 8.192(1.6);8.154(0.9); 7.937(0.8); 7.910(4.3); 7.898(8.3); 7.885(5.1); 7.837(5.4);7.825(9.3); 7.813(6.0); 7.583(0.8); 7.525(6.1); 7.516(7.8); 7.513(7.9);7.505(6.3); 7.451(9.5); 7.439(8.9); 7.263(66.7); 7.086(0.4); 5.301(4.1);4.129(1.1); 4.112(3.4); 4.094(4.4); 4.072(3.5); 4.055(1.2); 3.882(0.3);3.859(0.5); 3.841(0.4); 3.642(0.4); 3.625(0.5); 3.597(1.4); 3.580(3.6);3.564(4.4); 3.558(4.0); 3.541(3.2); 3.525(1.1); 3.490(0.5);1.577(178.8); 1.426(0.4); 1.371(1.1); 1.333(2.4); 1.285(4.4);1.256(10.6); 1.104(0.5); 0.881(1.6); 0.842(1.6); 0.070(0.6); 0.000(47.7)

Preparation Example 21:6-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-2-(5-fluoropyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(74) Step 1:4-Amino-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(5-fluoropyridin-3-yl)-1,3-thiazole-5-carboxamide(II-73)

Under argon, 2.8 ml of a 2M trimethylaluminium solution (5.61 mmol) intoluene were slowly added dropwise with ice cooling to 1.34 g (5.61mmol) of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]aniline in50 ml of 1,2-dichloroethane, and the mixture was stirred at roomtemperature for 1 hour. 500 mg (1.87 mmol) of ethyl4-amino-2-(5-fluoropyridin-3-yl)-1,3-thiazole-5-carboxylate (III-2) werethen added, and the reaction mixture was subsequently heated underreflux overnight. After cooling, the reaction mixture was carefullydischarged into a 10% potassium sodium tartrate solution (about 120 ml).The mixture was extracted three times with methylene chloride, and thecombined organic phases were dried over magnesium sulphate, filtered andconcentrated. The residue was stirred with a little acetonitrile to givea suspension. The insoluble fraction was filtered off with suction,washed with n-pentane and dried. This gave 330 mg (98.0% pure, 37.6% oftheory) of the title compound (II-73).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.613(4.5); 8.971(2.3); 8.968(4.0);8.770(3.9); 8.763(4.1); 8.155(1.2); 8.150(1.6); 8.144(1.2); 8.132(1.3);8.127(1.7); 8.120(1.2); 7.705(3.1); 7.686(3.1); 7.273(2.8); 7.245(2.8);7.208(5.1); 4.259(0.3); 4.241(0.3); 3.903(2.7); 3.875(4.0); 3.849(4.2);3.823(1.4); 3.329(26.3); 2.672(0.4); 2.668(0.3); 2.525(1.0);2.512(24.8); 2.507(49.6); 2.503(65.4); 2.499(49.2); 2.407(16.0);2.334(0.3); 2.330(0.4); 2.325(0.3); 1.297(0.4); 1.279(0.7); 1.262(0.3);0.008(1.0); 0.000(27.4); −0.008(1.2)

Step 2:6-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(5-fluoropyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(73)

200 mg (98% pure, 0.43 mmol) of4-amino-N-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(5-fluoropyridin-3-yl)-1,3-thiazole-5-carboxamide(II-73) were initially charged in 1 ml of N,N-dimethylacetamide. 37 mg(0.21 mmol) of p-toluenesulphonic acid and 189 mg (1.28 mmol) oftriethyl orthoformate were added thereto and the reaction mixture washeated at 130° C. in a CEM Discover microwave at 200 watts for 30minutes. The cooled reaction mixture was concentrated under high vacuumand purified by MPLC using the mobile phase acetonitrile/water. Thisgave 50 mg (97.0% pure, 24.2% of theory) of the title compound (73).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.243(3.5); 8.875(3.5); 8.868(3.6);8.693(7.7); 8.535(1.2); 8.530(1.7); 8.524(1.2); 8.512(1.2); 8.507(1.7);8.501(1.1); 7.940(3.1); 7.922(3.1); 7.521(2.7); 7.494(2.7); 4.061(1.2);4.035(3.8); 4.009(3.9); 3.984(1.4); 3.329(53.8); 2.676(0.3); 2.672(0.5);2.668(0.3); 2.507(49.1); 2.503(64.3); 2.499(49.1); 2.471(16.0);2.414(0.5); 2.334(0.3); 2.330(0.4); 2.325(0.3); 2.076(14.3); 1.233(0.9);0.000(0.4)

Step 3:6-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-2-(5-fluoropyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(74)

At 0° C., 42 mg (77% strength, 0.19 mmol) of meta-chloroperbenzoic acidwere added to a solution of 96.0 mg (0.19 mmol) of6-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-methyl-2-(5-fluoropyridin-3-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(73) in 1 ml of dichloromethane. The reaction mixture was stirred atroom temperature for 1 hour, and saturated sodium carbonate solution wasthen added. The aqueous phase was extracted three times withdichloromethane, and the combined organic phases were dried andfiltered. After evaporation of the solvent, the residue was thenpurified chromatographically by MPLC using the mobile phasecyclohexane/ethyl acetate. This gave 65 mg (94.0% pure, 68.4% of theory)of the title compound (74).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.249(4.3); 9.246(7.4); 9.242(4.4);8.876(7.8); 8.870(8.1); 8.738(16.0); 8.538(2.5); 8.533(3.1); 8.531(3.1);8.527(2.4); 8.515(2.6); 8.510(3.3); 8.503(2.4); 8.447(0.5); 8.317(0.7);8.200(6.2); 8.182(6.2); 7.639(4.3); 7.613(4.3); 5.758(2.5); 4.299(0.6);4.266(1.0); 4.241(0.8); 4.147(0.4); 4.126(0.7); 4.099(0.8); 4.038(0.5);4.020(0.4); 3.568(3.3); 3.329(336.9); 2.676(1.4); 2.671(2.0);2.667(1.5); 2.525(5.0); 2.520(7.9); 2.511(110.1); 2.507(225.1);2.502(308.8); 2.498(233.4); 2.494(111.7); 2.377(1.3); 2.334(1.5);2.329(2.0); 2.325(1.5); 1.989(1.2); 1.234(0.4); 1.207(0.4); 1.193(0.6);1.189(0.7); 1.175(0.8); 1.157(0.3); 0.000(0.9)

Preparation Example 22:6-{2,4-Dimethyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-2-(pyrimidin-5-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(77) Step 1:4-Amino-N-{2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyrimidin-5-yl)-1,3-thiazole-5-carboxamide(II-76)

Under argon, 2.1 ml of a 2M trimethylaluminium solution (4.20 mmol) intoluene were slowly added dropwise with ice cooling to 987 mg (4.20mmol) of 2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulphanyl]aniline in 70ml of 1,2-dichloroethane, and the mixture was stirred at roomtemperature for 1 hour. 350 mg (1.40 mmol) of ethyl4-amino-2-(pyrimidin-5-yl)-1,3-thiazole-5-carboxylate (III-3) were thenadded, and the reaction mixture was subsequently heated under refluxovernight. After cooling, the reaction mixture was carefully dischargedinto a 10% potassium sodium tartrate solution (about 120 ml). Themixture was extracted three times with methylene chloride, and thecombined organic phases were dried over magnesium sulphate, filtered andconcentrated. The residue was stirred with a little acetonitrile to givea suspension. The insoluble fraction was filtered off with suction,washed with n-pentane and dried. This gave 215 mg (90.0% pure, 31.5% oftheory) of the title compound (II-76).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.410(4.5); 9.327(6.4); 9.285(1.2);9.247(11.7); 7.465(5.7); 7.176(7.8); 7.170(7.4); 6.814(0.5); 6.793(0.6);5.754(0.7); 4.743(0.5); 4.264(0.5); 4.246(0.5); 3.875(1.3); 3.849(4.0);3.823(4.1); 3.798(1.5); 3.691(0.5); 3.666(0.5); 3.320(121.1);2.671(1.0); 2.502(151.6); 2.418(0.3); 2.367(15.3); 2.329(1.4);2.205(1.9); 2.162(16.0); 2.074(0.8); 2.000(1.8); 1.300(0.5); 1.282(1.1);1.265(0.6); 0.147(0.4); 0.000(72.2); −0.149(0.4)

Step 2:6-{2,4-Dimethyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyrimidin-5-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(76)

5 ml (30.1 mmol) of triethyl orthoformate were added to 100 mg (0.23mmol) of4-amino-N-{2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyrimidin-5-yl)-1,3-thiazole-5-carboxamide(II-76) and 20 mg (0.11 mmol) of p-toluenesulphonic acid and thereaction mixture was heated at 150° C. in a CEM Discover microwave for40 min. The cooled reaction mixture was concentrated under reducedpressure and then purified chromatographically by MPLC. This gave 36 mg(94.0% pure, 33.1% of theory) of the title compound (76).

1H-NMR (400.0 MHz, d6-DMSO): δ=9.538(16.0); 9.429(7.5); 8.559(8.5);7.680(4.9); 7.362(3.9); 5.754(1.8); 4.034(1.0); 4.008(2.9); 3.982(3.1);3.956(1.1); 3.318(38.5); 2.671(0.4); 2.524(1.0); 2.511(23.9);2.506(47.7); 2.502(62.3); 2.497(45.4); 2.493(22.1); 2.411(12.3);2.368(0.6); 2.329(0.4); 2.170(0.5); 2.080(13.3); 1.352(1.1); 1.336(0.4);1.259(0.4); 1.250(0.6); 1.229(1.2); 0.000(3.8)

Step 3:6-{2,4-Dimethyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-2-(pyrimidin-5-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(77)

At 0° C., 33 mg (77% strength, 0.15 mmol) of meta-chloroperbenzoic acidwere added to a solution of 70.0 mg (0.15 mmol) of6-{2,4-dimethyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-2-(pyrimidin-5-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(6H)-one(76) in 3 ml of dichloromethane. The reaction mixture was stirred in thecold for another 1 hour and then at room temperature overnight. Thereaction was washed successively with saturated sodium bisulphitesolution, sodium bicarbonate solution and sodium chloride solution,dried and concentrated. The residue was then purifiedchromatographically by MPLC. This gave 20 mg (97.0% pure, 28.7% oftheory) of the title compound (77).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.542(16.0); 9.429(7.8); 8.612(8.8);7.949(4.1); 7.939(2.8); 7.497(2.0); 7.471(3.0); 5.754(0.9); 4.321(0.4);4.293(0.5); 4.284(0.5); 4.257(0.5); 4.175(0.4); 4.166(0.4); 4.148(1.1);4.139(1.1); 4.121(1.1); 4.112(1.2); 4.094(0.4); 4.085(0.4); 3.969(0.5);3.942(0.5); 3.932(0.4); 3.905(0.5); 3.317(54.5); 2.675(0.5); 2.671(0.7);2.666(0.5); 2.506(79.6); 2.502(106.3); 2.497(82.4); 2.452(8.0);2.447(10.7); 2.338(0.5); 2.333(0.6); 2.328(0.7); 2.324(0.6); 2.258(0.4);2.188(10.5); 2.182(8.0); 1.234(0.7); 0.008(0.5); 0.000(13.1)

Synthesis of Aminothiazoles of the Formula (III) by Process B

Preparation Example 9: Ethyl4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate (III-1) Step 1:Ethyl 4-hydroxy-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate (VI-1)

32.5 g (235.2 mmol) of pyridine-3-carbothioamide were initially chargedin 200 ml of ethanol, and 58.5 g (244.6 mmol) of diethyl bromomalonatewere added. The mixture was heated under reflux overnight and thencooled and filtered. The filter residue was washed thoroughly withethanol and dried under reduced pressure. This gave 26.0 g (83.0% pure,36.7% of theory) of the title compound (VI-1).

1H-NMR (399.9 MHz, d₆-DMSO): δ=9.150 (2.8); 9.145 (2.8); 8.771 (1.9);8.768 (2.0); 8.759 (2.0); 8.756 (2.0); 8.399 (1.1); 8.395 (1.7); 8.390(1.3); 8.379 (1.3); 8.375 (1.8); 7.670 (1.6); 7.657 (1.7); 7.649 (1.7);7.637 (1.5); 7.249 (13.6); 7.121 (14.1); 6.993 (13.7); 4.695 (0.3);4.673 (0.4); 4.609 (0.4); 4.597 (0.5); 4.584 (0.5); 4.578 (0.5); 4.559(0.5); 4.507 (0.6); 4.498 (0.6); 4.488 (0.6); 4.475 (0.6); 4.459 (0.6);4.441 (0.7); 4.435 (0.7); 4.404 (0.7); 4.397 (0.7); 4.387 (0.8); 4.369(0.8); 4.351 (0.7); 4.335 (0.7); 4.294 (3.1); 4.276 (8.4); 4.259 (8.5);4.241 (3.1); 4.111 (0.4); 4.089 (0.3); 4.071 (0.3); 2.533 (0.5); 2.504(7.3); 2.500 (14.4); 2.495 (20.1); 2.490 (14.7); 2.486 (7.6); 1.306(7.9); 1.288 (16.0); 1.270 (7.7); 1.064 (0.5); 0.000 (2.3)

Step 2: Ethyl2-(pyridin-3-yl)-4-{[(trifluoromethyl)sulphonyl]oxy}-1,3-thiazole-5-carboxylate(V-1)

Under argon, 500 mg (2 mmol) of dry ethyl4-hydroxy-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate (VI-1) and 414 g(3 mmol) of potassium carbonate were initially charged indichloromethane at room temperature. 620 mg (2.2 mmol) oftrifluoromethanesulphonic anhydride were added dropwise over 10 minutesand the mixture was stirred at room temperature overnight. The mixturewas then washed with saturated sodium bicarbonate solution, the organicphase was filtered through a little Celite, the filter cake was washedwith dichloromethane and the filtrate was dried over sodium sulphate.Purification of the residue obtained after concentration was thencarried out by MPLC using a gradient of the mobile phasecyclohexane/ethyl acetate. This gave 220 mg (100.0% pure, 28.7% oftheory) of the title compound (V-1).

1H-NMR (399.9 MHz, d₆-DMSO): δ=3.115 (16.0); 2.498 (0.9); 2.493 (1.8);2.489 (2.5); 2.484 (1.8); 2.479 (0.9); 1.341 (0.5)

Step 3: Ethyl4-(benzylamino)-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate (IV-1)

20.0 g (52.0 mmol) of ethyl2-(pyridin-3-yl)-4-{[(trifluoromethyl)sulphonyl]oxy}-1,3-thiazole-5-carboxylate(V-1) and 11.2 g (104.1 mmol) of benzylamine in 100 ml of dioxane werestirred under reflux overnight. After cooling and concentration of thereaction mixture, methanol was added to the oily residue and theprecipitated yellow solid was filtered off with suction and washed withpentane. Excess benzylamine in the crude product was subsequentlyremoved by washing with 1 N hydrochloric acid. The crude product wasthen washed with water, stirred with pentane, filtered off with suctionand dried under reduced pressure. This gave 13.5 g (100% pure, 76.4% oftheory) of the title compound (IV-1).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.153(4.6); 9.148(4.9); 8.745(3.2);8.742(3.3); 8.733(3.3); 8.730(3.1); 8.374(1.6); 8.370(2.5); 8.366(1.7);8.354(1.9); 8.350(2.7); 7.618(3.8); 7.605(3.4); 7.597(2.9); 7.585(2.4);7.413(4.4); 7.394(7.2); 7.347(4.0); 7.329(7.1); 7.309(3.6); 7.251(2.2);7.233(3.1); 7.215(1.1); 4.780(4.8); 4.767(4.8); 4.285(2.3); 4.267(7.3);4.249(7.4); 4.232(2.5); 4.039(0.4); 4.021(0.4); 3.913(2.0); 3.775(0.7);3.760(0.7); 3.744(0.7); 2.509(41.8); 2.505(53.2); 2.501(40.7);2.332(0.4); 1.990(1.1); 1.297(7.8); 1.280(16.0); 1.262(7.6); 1.176(0.6);0.000(6.0)

Step 4: Ethyl 4-amino-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate(III-1)

40 ml of concentrated sulphuric acid were initially charged and 8.5 g(25.0 mmol) of ethyl4-(benzylamino)-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylate (IV-1) wereadded slowly at 20° C. The reaction mixture was stirred at roomtemperature for 3 h and then added to 500 ml of ice-water, and the pHwas adjusted carefully to pH 10 using 30% strength potassium hydroxidesolution. The mixture was then extracted with ethyl acetate, and theorganic phases were dried and concentrated. This gave 6.0 g (100% pure,96.1% of theory) of the title compound (III-1).

1H-NMR (400.0 MHz, ds-DMSO): δ=9.113(4.3); 9.109(4.3); 9.107(4.3);8.730(3.0); 8.727(3.4); 8.718(3.3); 8.715(3.4); 8.296(1.7); 8.291(2.6);8.286(1.9); 8.276(1.8); 8.271(2.7); 8.266(2.0); 7.578(2.4); 7.566(2.5);7.558(2.4); 7.546(2.3); 7.139(3.5); 4.271(2.4); 4.253(7.5); 4.236(7.6);4.218(2.5); 3.333(25.6); 2.504(43.0); 2.500(34.6); 1.990(0.5);1.296(7.8); 1.278(16.0); 1.261(7.7); 0.000(0.6)

Preparation Example 23: Ethyl4-amino-2-(5-fluoropyridin-3-yl)-1,3-thiazole-5-carboxylate (III-2) Step1: Ethyl 2-(5-fluoropyridin-3-yl)-4-hydroxy-1,3-thiazole-5-carboxylate(VI-2)

38.6 g (247 mmol) of 5-fluoropyridine-3-carbothioamide were initiallycharged in 250 ml of ethanol, and 60 ml of pyridine and 177.3 g (741mmol) of diethyl bromomalonate were then added. The mixture was heatedunder reflux overnight and then cooled and filtered. The filter residuewas washed thoroughly with ethanol and dried under reduced pressure.This gave 37.0 g (94.9% pure, 53.0% of theory) of the title compound(VI-2).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.013(4.9); 8.765(4.9); 8.758(5.0);8.227(1.6); 8.221(2.1); 8.216(1.6); 8.204(1.6); 8.198(2.1); 8.193(1.5);4.275(2.3); 4.258(7.3); 4.240(7.4); 4.222(2.4); 3.324(2.6); 2.508(32.1);2.504(41.6); 2.500(31.7); 1.294(7.8); 1.276(16.0); 1.259(7.6);0.000(3.7)

Step 2: Ethyl2-(5-fluoropyridin-3-yl)-4-{[(trifluoromethyl)sulphonyl]oxy}-1,3-thiazole-5-carboxylate(V-2)

Under argon, 37.0 g (138 mmol) of ethyl2-(5-fluoropyridin-3-yl)-4-hydroxy-1,3-thiazole-5-carboxylate (VI-2)were initially charged in 300 ml of dichloromethane, 45 ml of pyridinewere added and the reaction was cooled to 0° C. Thereafter, 54.5 g (193mmol) of trifluoromethanesulphonic anhydride were slowly added dropwise,and the mixture was stirred at room temperature overnight. The reactionsolution was filtered, the filter residue was washed withdichloromethane and the filtrate was concentrated. The residue obtainedwas warmed with 400 ml of methyl tert-butyl ether (MTBE) at 55° C. for30 min and decanted while still warm. This procedure was repeated with afurther 300 ml of MTBE. The combined MTBE fractions were concentratedand the residue obtained was dried under reduced pressure. This gave55.8 g (98.6% pure, 99.6% of theory) of the title compound (V-2).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.083(2.7); 9.079(4.5); 9.076(2.7);8.849(4.5); 8.842(4.5); 8.364(1.5); 8.359(1.9); 8.357(1.9); 8.353(1.5);8.341(1.6); 8.336(2.0); 8.334(1.8); 8.329(1.4); 4.427(2.2); 4.409(7.2);4.392(7.3); 4.374(2.3); 3.569(13.3); 3.344(8.3); 2.672(0.3); 2.526(0.8);2.512(19.0); 2.508(38.3); 2.503(50.2); 2.499(37.2); 2.494(18.6);2.330(0.3); 1.355(7.6); 1.337(16.0); 1.319(7.4); 0.000(3.2)

Step 3: Ethyl4-(benzylamino)-2-(5-fluoropyridin-3-yl)-1,3-thiazole-5-carboxylate(IV-2)

55.8 g (139 mmol) of ethyl2-(5-fluoropyridin-3-yl)-4-{[(trifluoromethyl)sulphonyl]oxy}-1,3-thiazole-5-carboxylate(V-1) and 29.7 g (277 mmol) of benzylamine in 300 ml of dioxane werestirred under reflux overnight. After cooling and concentration of thereaction mixture, methanol was added to the oily residue and theprecipitated yellow solid was filtered off with suction and washed withpentane. Excess benzylamine in the crude product was subsequentlyremoved by washing with 1 N hydrochloric acid. The crude product wasthen washed with water, stirred with pentane, filtered off with suctionand dried under reduced pressure. This gave 42.6 g (100% pure, 85.9% oftheory) of the title compound (IV-2).

1H-NMR (400.0 MHz, d₆-DMSO): δ=9.015(2.9); 9.011(4.9); 8.746(4.6);8.740(4.7); 8.249(1.5); 8.244(1.9); 8.242(1.9); 8.238(1.5); 8.225(1.6);8.220(2.0); 8.214(1.5); 7.628(1.1); 7.612(2.3); 7.596(1.2); 7.444(0.4);7.411(4.0); 7.393(6.2); 7.344(3.6); 7.340(1.3); 7.326(6.6); 7.307(3.3);7.249(2.0); 7.231(2.8); 7.213(1.0); 4.782(5.7); 4.766(5.7); 4.289(2.2);4.271(7.1); 4.253(7.3); 4.236(2.3); 4.029(0.5); 3.568(0.4); 3.318(32.2);2.676(0.4); 2.671(0.6); 2.667(0.4); 2.524(1.1); 2.511(33.4);2.507(65.6); 2.502(85.2); 2.498(63.3); 2.494(31.8); 2.333(0.4);2.329(0.6); 2.324(0.4); 1.298(7.6); 1.280(16.0); 1.262(7.5); 0.146(0.4);0.008(3.4); 0.000(85.6); −0.008(3.8); −0.019(0.4); −0.150(0.4)

Step 4: Ethyl4-amino-2-(5-fluoropyridin-3-yl)-1,3-thiazole-5-carboxylate (III-2)

3 ml of concentrated sulphuric acid were initially charged and 500 mg(1.39 mmol) of ethyl4-(benzylamino)-2-(5-fluoropyridin-3-yl)-1,3-thiazole-5-carboxylate(IV-2) were added slowly at 20° C. The reaction mixture was stirred atroom temperature overnight and then added to 10 ml of ice-water, and thepH was adjusted carefully to pH 10 using 30% strength potassiumhydroxide solution. The mixture was then extracted with ethyl acetate,and the organic phases were dried over magnesium sulphate andconcentrated. The residue was triturated with n-pentane, filtered anddried. This gave 200 mg (100% pure, 53.5% of theory) of the titlecompound (III-2).

1H-NMR (400.0 MHz, d6-DMSO): δ=8.994(6.0); 8.757(5.4); 8.750(5.8);8.193(2.8); 8.170(2.8); 7.143(4.8); 4.278(2.6); 4.260(7.7); 4.242(7.8);4.225(2.7); 3.319(18.0); 2.673(0.3); 2.504(52.6); 2.331(0.3);1.298(8.1); 1.280(16.0); 1.263(7.9); 0.000(11.1)

Further compounds of the formula (I) are compiled in the table whichfollows.

TABLE 1 Compounds of the formula (I)

Compound No. Het A Q V R¹ 1

S CH O

2

S CH O

3

S CH O

4

S CH O

5

S CH O

6

S CH O

7

S CH O

8

S CH O

9

S CH O

10

S CH O

11

S CH O

12

S CH O

13

S CH O

14

S CH O

15

S CH O

16

S CH O

17

S CH O

18

S CH O

19

S CH O

20

S CH O

21

S CH O

22

S CH O

23

S CH O

24

S CH O

25

S CH O

26

S CH O

27

S CH O

28

S CH O

32

S CH O

34

S CH O

35

S CH O

36

S CH O

37

S CH O

38

S CH O

39

S CH O

40

S CH O

41

S CH O

42

S CH O

43

S CH O

44

S CH O

45

S CH O

46

S CH O

47

S CH O

48

S CH O

49

S CH O

50

S CH O

51

S CH O

52

S CH O

53

S CH O

54

S CH O

55

S CH O

56

S C—CH3 O

57

S C—CH3 O

58

S N O

59

S N O

60

S CH O

61

S CH O

62

S CH O

63

S CH O

64

S CH O

65

S CH O

66

S CH O

67

S CH O

68

S CH O

69

S CH O

70

S CH O

71

S CH O

72

S CH O

73

S CH O

74

S CH O

75

S CH O

76

S CH O

77

S CH O

78

S CH O

79

S CH O

80

S C—CH3 O

81

S CH O

82

S CH O

83

S CH O

84

S CH O

85

S CH O

86

S CH O

TABLE 2 Analytical data for the compounds reported Ex. No. logP[a]logP[b] 1H-NMR [σ (ppm)] or LC-MS [m/z] 1 1.35 1.43 1H-NMR(400.0 MHz,d₆-DMSO): δ = 9.307(2.2); 9.302(2.2); 8.814(1.6); 8.811(1.7);8.802(1.7); 8.799(1.7); 8.734(6.2); 8.516(1.0); 8.512(1.3); 8.506(1.0);8.496(1.1); 8.491(1.4); 8.486(1.0); 8.144(3.9); 7.659(1.3); 7.647(1.3);7.641(1.3); 7.639(1.3); 7.628(1.2); 7.627(1.2); 5.054(0.4); 5.037(1.1);5.019(1.5); 5.002(1.1); 4.985(0.4); 3.337(1.4); 2.526(0.8); 2.513(17.3);2.508(34.7); 2.504(45.2); 2.499(32.4); 2.495(15.5); 1.483(16.0);1.466(15.8); 1.142(0.4); 1.126(0.4); 0.000(8.5) 2 1.05 LC-MS: mass found[m/z] = 270.06 3 1.70 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.302(2.1);9.297(2.1); 9.049(0.4); 9.044(0.4); 8.815(1.8); 8.811(1.9); 8.803(1.8);8.799(1.8); 8.703(0.3); 8.699(0.4); 8.691(0.4); 8.687(0.4); 8.634(6.2);8.510(1.1); 8.506(1.4); 8.500(1.1); 8.490(1.1); 8.486(1.4); 8.484(1.4);8.480(1.1); 7.662(1.3); 7.660(1.4); 7.650(1.3); 7.648(1.3); 7.642(1.3);7.640(1.3); 7.630(1.2); 7.628(1.3); 6.974(0.7); 3.895(4.7); 3.876(4.7);3.323(24.1); 3.022(0.4); 3.005(0.6); 2.990(0.4); 2.512(10.6);2.508(21.2); 2.503(27.9); 2.499(20.3); 2.495(10.0); 2.162(0.4);2.145(0.8); 2.128(1.0); 2.111(0.9); 2.093(0.4); 0.916(16.0);0.899(15.5); 0.873(3.2); 0.856(3.1); 0.008(0.3); 0.000(8.4); −0.008(0.3)4 1.19 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.317(7.3); 9.313(7.0);9.064(1.2); 9.060(1.2); 8.824(5.6); 8.820(6.0); 8.812(5.9); 8.808(5.8);8.719(0.9); 8.716(1.0); 8.707(1.0); 8.704(0.9); 8.642(16.0); 8.527(3.3);8.522(4.3); 8.517(3.2); 8.507(3.5); 8.502(4.6); 8.497(3.3); 8.317(0.5);8.238(0.7); 8.233(1.1); 8.229(0.7); 8.218(1.3); 8.214(1.0); 8.208(0.8);8.149(2.5); 7.666(4.2); 7.654(4.2); 7.646(4.1); 7.636(3.8); 7.634(3.9);7.586(0.7); 7.574(0.7); 7.566(0.6); 7.554(0.6); 7.101(2.0); 6.573(1.0);6.564(2.0); 6.555(0.9); 6.436(2.0); 6.427(4.2); 6.418(1.9); 6.298(1.0);6.289(2.1); 6.280(1.0); 6.077(0.6); 5.937(0.3); 4.626(3.1); 4.617(3.4);4.589(6.9); 4.580(6.7); 4.551(3.5); 4.542(3.3); 3.622(0.4); 3.611(0.3);3.597(0.6); 3.583(0.7); 3.573(0.6); 3.559(0.3); 3.545(0.4); 3.334(26.6);2.677(0.6); 2.673(0.8); 2.669(0.6); 2.526(1.7); 2.513(45.8);2.508(92.2); 2.504(120.6); 2.500(86.8); 2.495(41.6); 2.335(0.6);2.331(0.8); 2.326(0.6); 2.288(0.5); 0.008(0.6); 0.000(15.7); −0.009(0.6) 5 1.54 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.320(8.2); 9.315(8.2);9.302(0.4); 8.829(6.4); 8.825(6.8); 8.817(6.9); 8.813(6.6); 8.698(16.0);8.530(4.0); 8.526(5.1); 8.520(3.9); 8.510(4.3); 8.506(5.3); 8.505(5.3);8.500(4.0); 8.318(0.4); 7.672(4.8); 7.671(4.8); 7.660(4.8); 7.659(4.7);7.652(4.8); 7.651(4.6); 7.640(4.5); 7.639(4.4); 5.143(0.3); 5.121(0.4);5.089(3.5); 5.067(11.4); 5.044(11.9); 5.021(4.0); 3.363(0.6);3.336(289.1); 2.720(1.5); 2.678(0.6); 2.674(0.8); 2.669(0.6);2.527(2.1); 2.513(48.7); 2.509(96.7); 2.505(125.4); 2.500(89.6);2.496(42.7); 2.336(0.6); 2.331(0.8); 2.327(0.6); 2.077(0.4); 0.008(1.2);0.000(30.0); −0.008(1.1) 6 1.57 1H-NMR(400.0 MHz, d₆-DMSO): δ =9.313(4.1); 9.308 (4.1); 8.818 (2.9); 8.809 (2.9); 8.806 (3.0); 8.789(13.6); 8.521 (2.0); 8.517 (2.8); 8.511 (2.1); 8.501 (2.3); 8.496 (3.3);8.491 (4.6); 8.477 (3.1); 7.841 (1.8); 7.837 (1.8); 7.822 (3.6); 7.818(3.7); 7.803 (2.1); 7.798 (2.1); 7.666 (2.5); 7.654 (2.5); 7.646 (2.4);7.634 (2.3); 7.478 (4.2); 7.458 (3.8); 7.333 (2.2); 7.321 (2.3); 7.316(2.3); 7.304 (2.0); 5.399 (16.0); 3.904 (5.6); 3.508 (0.3); 3.477 (0.4);3.455 (0.5); 3.354 (684.8); 3.268 (0.4); 3.175 (0.6); 3.162 (0.6); 2.678(0.9); 2.673 (1.3); 2.669 (1.0); 2.526 (3.9); 2.513 (80.9); 2.509(159.9); 2.504 (207.8); 2.500 (153.1); 2.496 (77.4); 2.335 (0.9); 2.331(1.2); 2.327 (0.9); 1.234 (0.5); 0.008 (0.5); 0.000 (16.1); −0.008 (0.6)7 0.65 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.317(2.0); 9.312(2.1);8.821(1.7); 8.817(1.8); 8.809(1.8); 8.805(1.7); 8.525(1.0); 8.521(1.4);8.516(1.1); 8.501(7.3); 7.667(1.3); 7.655(1.3); 7.647(1.3); 7.635(1.2);5.010(7.5); 3.320(48.4); 3.297(0.4); 3.104(16.0); 2.884(14.6);2.670(0.4); 2.540(0.3); 2.506(47.9); 2.502(61.3); 2.497(44.5);2.328(0.4); 0.008(0.8); 0.000(16.9); −0.008(0.8) 8 1.94 1.941H-NMR(400.0 MHz, d₆-DMSO): δ = 9.342(3.0); 9.337(2.9); 8.832(2.2);8.828(2.5); 8.820(2.4); 8.816(2.5); 8.612(9.7); 8.553(1.3); 8.548(1.7);8.543(1.4); 8.533(1.4); 8.527(1.8); 8.523(1.4); 7.678(1.8); 7.666(1.7);7.658(1.7); 7.646(1.6); 7.497(1.3); 7.477(2.7); 7.459(2.4); 7.398(3.1);7.381(4.4); 7.362(3.0); 5.758(0.5); 3.327(46.7); 2.676(0.4); 2.671(0.6);2.667(0.4); 2.525(1.4); 2.520(2.2); 2.511(31.8); 2.507(65.7);2.502(87.7); 2.498(64.6); 2.493(31.9); 2.402(16.0); 2.333(0.4);2.329(0.6); 2.325(0.4); 2.309(0.5); 1.299(0.5); 1.259(0.7); 1.233(0.9);1.183(0.3); 0.146(0.5); 0.008(3.7); 0.000(106.2); −0.009(3.7);−0.150(0.5) 9 2.26 2.23 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.352(4.9);9.346(4.8); 8.836(3.7); 8.833(4.1); 8.824(4.0); 8.821(4.1); 8.707(16.0);8.563(2.1); 8.558(2.8); 8.553(2.2); 8.543(2.3); 8.537(3.1); 8.533(2.2);8.089(5.0); 7.953(3.6); 7.933(6.0); 7.868(3.1); 7.848(3.3); 7.829(1.4);7.681(2.8); 7.669(2.8); 7.661(2.7); 7.650(2.5); 7.649(2.7); 4.038(0.5);4.020(0.5); 3.328(60.0); 2.944(5.2); 2.784(4.1); 2.676(0.4); 2.672(0.5);2.667(0.4); 2.525(1.3); 2.512(28.1); 2.507(57.8); 2.503(77.3);2.498(57.0); 2.494(28.2); 2.334(0.4); 2.329(0.5); 2.325(0.4);1.989(2.2); 1.957(4.3); 1.193(0.9); 1.175(1.3); 1.157(0.6); 0.008(2.3);0.000(68.3); −0.009(2.6) 10 1.73 1.76 1H-NMR(400.0 MHz, d₆-DMSO): δ =9.345(0.5); 9.340(0.5); 8.833(0.4); 8.829(0.4); 8.821(0.4); 8.817(0.4);8.620(1.4); 7.495(0.6); 7.475(0.4); 7.217(0.3); 7.211(0.6); 7.206(0.4);7.155(0.4); 7.134(0.5); 3.818(3.8); 3.328(15.7); 2.944(16.0);2.784(13.5); 2.507(16.3); 2.502(21.3); 2.498(16.0); 1.957(14.1);0.008(1.0); 0.000(24.1); −0.008(1.1) 11 1.92 1.96 1H-NMR(400.0 MHz,d₆-DMSO): δ = 9.341(3.2); 9.336(3.1); 8.831(2.4); 8.827(2.6);8.819(2.5); 8.815(2.6); 8.598(10.7); 8.552(1.4); 8.547(1.9); 8.542(1.4);8.532(1.5); 8.526(2.0); 8.522(1.4); 8.317(0.4); 7.677(1.9); 7.665(1.8);7.657(1.8); 7.645(1.8); 7.462(4.1); 7.442(8.2); 7.399(6.4); 7.378(3.3);5.758(0.4); 3.325(150.9); 2.675(1.1); 2.671(1.5); 2.666(1.2);2.524(3.5); 2.510(82.2); 2.506(170.6); 2.502(229.7); 2.497(169.6);2.493(83.7); 2.408(16.0); 2.333(1.1); 2.328(1.5); 2.324(1.1);1.298(0.7); 1.258(1.0); 1.234(1.3); 0.000(2.4) 12 1.73 1.76 1H-NMR(400.0MHz, d₆-DMSO): δ = 8.591(0.4); 3.841(1.0); 3.328(7.1); 2.945(16.0);2.784(13.9); 2.506(6.9); 2.502(8.5); 2.498(6.5); 1.958(14.6); 0.000(5.1)13 2.09 2.08 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.344(5.3); 9.340(5.4);8.829(4.0); 8.820(4.1); 8.631(16.0); 8.554(2.6); 8.550(3.8); 8.545(2.8);8.534(2.9); 8.529(4.0); 8.525(2.8); 8.150(2.0); 7.678(3.4); 7.666(3.5);7.658(3.5); 7.646(3.3); 7.534(2.8); 7.515(7.2); 7.495(13.4); 7.459(0.3);7.440(5.4); 7.420(3.2); 7.350(4.5); 7.329(3.5); 3.324(14.3); 2.859(0.4);2.768(0.4); 2.671(0.9); 2.554(1.1); 2.529(47.8); 2.506(102.3);2.502(131.0); 2.498(102.0); 2.476(2.9); 2.329(0.9); 1.295(0.3);1.278(0.6); 1.187(0.4); 0.000(38.9) 14 1.04 1.09 1H-NMR(400.0 MHz,d₆-DMSO): δ = 9.351(2.4); 9.346(2.2); 8.835(1.7); 8.832(1.8);8.823(1.8); 8.820(1.8); 8.721(1.4); 8.707(6.9); 8.561(1.1); 8.556(1.4);8.551(1.0); 8.541(1.2); 8.536(1.5); 8.531(1.0); 8.213(0.5); 8.208(0.3);8.152(0.6); 7.939(1.5); 7.935(2.7); 7.907(0.4); 7.888(0.5); 7.879(0.7);7.875(1.2); 7.871(0.8); 7.860(1.2); 7.856(2.2); 7.852(1.3); 7.828(1.2);7.808(2.5); 7.789(1.8); 7.786(1.7); 7.782(2.4); 7.777(1.5); 7.767(0.6);7.762(0.8); 7.758(0.4); 7.682(1.4); 7.670(1.3); 7.662(1.4); 7.650(1.3);5.756(0.7); 3.323(10.5); 3.314(5.1); 2.847(0.7); 2.837(16.0);2.671(0.4); 2.511(20.1); 2.507(40.7); 2.502(54.5); 2.498(41.2);2.494(21.4); 2.329(0.3); 0.146(0.4); 0.008(3.0); 0.000(74.0);−0.008(4.1); −0.150(0.3) 15 2.42 2.35 1H-NMR(601.6 MHz, d₆-DMSO): δ =9.357(2.9); 9.354(2.9); 9.353(2.8); 8.842(2.5); 8.839(2.6); 8.834(2.6);8.831(2.6); 8.636(10.4); 8.564(1.4); 8.561(1.9); 8.560(1.7); 8.557(1.4);8.551(1.5); 8.548(1.8); 8.547(1.9); 8.544(1.5); 7.686(1.7); 7.685(1.7);7.678(1.7); 7.677(1.7); 7.672(1.7); 7.671(1.7); 7.665(1.7); 7.663(1.7);7.403(3.7); 7.400(3.9); 7.393(2.6); 7.380(2.9); 7.266(2.3); 7.263(2.2);7.253(1.9); 7.249(1.9); 3.342(244.4); 2.955(1.3); 2.794(1.0);2.627(0.7); 2.625(1.0); 2.622(0.7); 2.534(1.7); 2.531(2.2); 2.528(2.4);2.519(52.0); 2.516(108.9); 2.513(148.0); 2.510(110.3); 2.507(54.0);2.500(25.7); 2.400(0.7); 2.397(1.0); 2.394(0.7); 2.327(16.0);2.297(0.4); 1.968(1.1) 16 1.25 1.26 1H-NMR(400.0 MHz, d₆-DMSO): δ =9.348(2.8); 9.343(2.8); 8.831(2.2); 8.819(2.3); 8.675(6.0); 8.554(1.7);8.534(1.8); 7.960(3.2); 7.956(3.2); 7.679(1.7); 7.667(2.9); 7.660(2.0);7.647(3.3); 7.541(2.8); 7.521(2.1); 3.326(55.5); 2.944(0.5);2.773(16.0); 2.690(0.5); 2.671(0.5); 2.502(76.7); 2.436(13.1);2.328(0.5); 2.301(0.4); 1.957(0.4); 1.234(0.6); 0.000(0.5) 17 2.70 2.661H-NMR(400.0 MHz, d₆-DMSO): δ = 9.353(5.0); 9.347(5.0); 8.837(3.7);8.833(4.2); 8.825(4.0); 8.821(4.2); 8.659(16.0); 8.563(2.1); 8.558(2.9);8.554(2.2); 8.543(2.2); 8.538(3.1); 8.534(2.3); 8.443(0.5); 8.317(0.6);8.187(2.6); 8.181(2.8); 8.172(2.7); 8.165(2.8); 7.993(1.6); 7.986(1.6);7.982(1.9); 7.975(1.8); 7.971(2.1); 7.964(2.1); 7.960(2.1); 7.953(1.9);7.773(3.5); 7.751(6.1); 7.729(2.9); 7.682(2.9); 7.669(2.8); 7.662(2.8);7.649(2.8); 5.758(0.5); 3.326(262.3); 2.675(2.1); 2.671(3.0);2.666(2.3); 2.524(7.8); 2.519(11.5); 2.511(161.4); 2.506(336.0);2.502(452.0); 2.497(336.0); 2.493(167.4); 2.333(2.1); 2.329(3.0);2.324(2.2); 1.298(0.6); 1.259(0.8); 1.234(1.2); 1.203(0.4); 1.185(0.8);1.167(0.4); 1.148(0.3); 0.146(2.7); 0.025(0.6); 0.008(19.5);0.000(584.9); −0.009(21.7); −0.150 (2.7) 18 2.01 1.95 1H-NMR(400.0 MHz,d₆-DMSO): δ = 9.347(0.3); 8.927(7.1); 8.670(16.0); 8.659(1.1);8.461(3.7); 8.459(3.6); 8.445(3.9); 8.443(3.8); 8.317(0.5); 8.182(3.0);8.175(3.3); 8.166(3.2); 8.160(3.1); 8.083(3.7); 8.063(4.1); 7.987(1.8);7.980(1.9); 7.976(2.1); 7.969(2.0); 7.965(2.4); 7.958(2.4); 7.954(2.4);7.947(1.9); 7.773(3.7); 7.751(6.6); 7.730(3.1); 7.665(3.7); 7.648(4.1);7.645(4.1); 7.628(3.2); 5.758(0.4); 3.325(270.0); 2.675(2.0);2.671(2.7); 2.667(2.1); 2.574(0.4); 2.506(313.6); 2.502(411.0);2.498(314.6); 2.333(1.9); 2.329(2.7); 2.324(2.0); 1.297(0.3);1.259(0.4); 1.235(1.5); 1.196(0.4); 1.178(0.7); 1.160(0.4); 0.146(1.4);0.008(11.9); 0.000(302.6); −0.150(1.5) 19 2.39 2.43 1H-NMR(400.0 MHz,d₆-DMSO): δ = 9.343(3.7); 9.338(3.7); 8.832(2.7); 8.828(3.0);8.820(2.9); 8.816(3.1); 8.633(11.2); 8.554(1.5); 8.549(2.2); 8.544(1.7);8.534(1.7); 8.528(2.3); 8.524(1.7); 8.316(0.7); 7.677(2.1); 7.665(2.1);7.657(2.1); 7.645(2.0); 7.545(2.7); 7.540(5.9); 7.519(4.3); 7.500(3.6);7.468(3.5); 7.448(1.7); 7.373(2.6); 7.357(1.6); 7.353(2.0); 3.324(30.1);3.083(2.3); 3.065(7.5); 3.046(7.6); 3.028(2.5); 2.945(1.3); 2.785(1.1);2.671(0.4); 2.525(1.0); 2.507(46.5); 2.502(62.8); 2.498(47.8);2.329(0.4); 1.957(1.1); 1.302(7.8); 1.284(16.0); 1.266(7.5); 0.008(2.3);0.000(63.4); −0.008(3.2) 20 1.24 1.26 1H-NMR(400.0 MHz, d₆-DMSO): δ =9.356(4.7); 9.351(4.7); 8.841(3.4); 8.838(3.6); 8.829(3.6); 8.826(3.6);8.735(0.5); 8.712(12.7); 8.566(2.0); 8.562(2.8); 8.557(2.0); 8.546(2.2);8.541(2.9); 8.537(2.0); 8.164(2.1); 7.889(5.6); 7.823(5.6); 7.821(5.6);7.814(4.9); 7.809(7.5); 7.797(1.3); 7.787(3.5); 7.782(2.9); 7.778(2.2);7.772(2.6); 7.764(1.0); 7.759(0.9); 7.687(2.6); 7.675(2.6); 7.667(2.6);7.655(2.5); 3.407(0.5); 3.388(0.7); 3.332(3.2); 3.172(0.5); 3.154(1.8);3.136(2.2); 3.120(2.5); 3.102(2.2); 3.084(0.7); 2.901(0.6); 2.883(2.2);2.864(2.5); 2.849(2.1); 2.830(1.8); 2.812(0.5); 2.679(0.4); 2.674(0.3);2.514(50.7); 2.510(65.6); 2.506(49.5); 2.341(0.3); 2.337(0.4);1.169(0.6); 1.106(7.5); 1.088(16.0); 1.070(7.3); 1.058(0.8) 21 2.95 2.911H-NMR(400.0 MHz, d₆-DMSO): δ = 9.350(3.0); 9.346(3.1); 9.344(3.0);8.839(2.4); 8.836(2.6); 8.827(2.6); 8.824(2.6); 8.679(8.7); 8.561(1.4);8.557(1.8); 8.551(1.4); 8.541(1.5); 8.537(1.9); 8.535(1.9); 8.531(1.5);7.939(3.1); 7.921(3.1); 7.684(1.8); 7.683(1.7); 7.672(1.7); 7.671(1.7);7.664(1.8); 7.663(1.7); 7.652(1.7); 7.651(1.7); 7.518(2.7); 7.491(2.6);4.062(1.2); 4.037(3.9); 4.011(4.0); 3.985(1.4); 3.330(57.6); 2.945(1.0);2.785(0.7); 2.672(0.4); 2.526(1.0); 2.512(19.8); 2.508(40.6);2.503(53.8); 2.499(39.4); 2.494(19.5); 2.471(16.0); 2.330(0.3);2.076(10.9); 1.958(0.8); 0.008(1.0); 0.000(30.1); −0.009(1.2) 22 2.011.98 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.761(0.5); 9.353(6.6); 9.347(6.9);9.102(0.4); 8.836(5.2); 8.828(4.9); 8.824(5.2); 8.738(0.5); 8.723(15.6);8.557(4.0); 8.553(2.9); 8.543(2.8); 8.537(4.3); 8.533(3.1); 8.315(2.5);8.195(6.5); 8.176(6.5); 8.039(0.4); 7.951(2.4); 7.685(3.8); 7.673(3.8);7.665(4.0); 7.653(3.8); 7.635(5.0); 7.608(5.1); 7.366(0.4); 7.238(0.6);5.755(1.0); 4.293(0.9); 4.271(1.2); 4.263(1.3); 4.233(1.1); 4.182(0.4);4.124(1.0); 4.100(1.2); 3.505(1.6); 3.322(748.9); 2.944(1.9);2.891(16.0); 2.784(1.6); 2.731(14.3); 2.716(0.5); 2.670(6.0);2.666(4.8); 2.505(695.9); 2.501(960.0); 2.497(767.5); 2.395(0.8);2.373(2.4); 2.328(6.2); 2.324(5.1); 2.283(0.4); 1.957(1.9); 1.303(0.3);1.284(0.6); 1.233(2.0); 0.854(0.4); 0.146(3.0); 0.008(21.8);0.000(638.0); −0.078(0.4); −0.150 (3.2) 23 1.49 1.45 1H-NMR(400.0 MHz,d₆-DMSO): δ = 8.928(9.2); 8.734(16.0); 8.463(5.2); 8.446(5.3);8.315(0.9); 8.196(7.0); 8.177(7.1); 8.082(5.1); 8.061(5.7); 7.668(4.5);7.649(5.9); 7.633(8.7); 7.608(5.6); 7.573(0.4); 7.251(0.4); 4.265(1.6);4.236(1.3); 4.117(1.2); 4.106(1.2); 4.092(1.4); 3.322(182.5);2.671(2.1); 2.502(339.3); 2.498(298.4); 2.402(0.7); 2.373(1.6);2.329(2.4); 0.146(1.6); 0.000(312.8); −0.083 (0.4); −0.150(1.7) 24 2.762.70 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.345(0.4); 9.340(0.4); 8.640(1.0);7.597(0.5); 7.539(0.3); 7.520(0.4); 7.512(0.4); 3.327(6.0); 2.945(16.0);2.785(13.5); 2.507(6.8); 2.503(9.0); 2.498(6.9); 1.989(0.6);1.958(14.1); 1.305(2.7); 1.289(2.7); 0.000(8.3); −0.008(0.4) 25 1.391.43 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.351(4.6); 9.347(4.5); 8.835(3.5);8.832(3.8); 8.823(3.7); 8.820(3.8); 8.727(0.5); 8.701(15.5); 8.562(2.1);8.558(2.7); 8.556(2.6); 8.552(2.1); 8.542(2.3); 8.538(2.7); 8.536(2.9);8.532(2.1); 8.317(0.3); 7.858(3.3); 7.853(5.8); 7.828(0.7); 7.821(0.4);7.810(2.1); 7.791(7.7); 7.788(7.6); 7.785(6.6); 7.783(5.9); 7.777(5.1);7.772(3.1); 7.765(1.1); 7.759(1.4); 7.754(1.0); 7.682(2.6); 7.680(2.6);7.670(2.5); 7.668(2.6); 7.662(2.5); 7.660(2.5); 7.650(2.4); 7.648(2.5);5.757(16.0); 3.325(116.5); 3.085(0.8); 3.068(2.2); 3.051(3.1);3.034(2.3); 3.016(0.9); 2.680(0.4); 2.676(0.9); 2.671(1.3); 2.667(0.9);2.524(3.1); 2.511(71.5); 2.507(145.1); 2.502(193.0); 2.498(144.3);2.493(72.7); 2.425(0.5); 2.333(1.0); 2.329(1.3); 2.324(1.0); 1.259(0.6);1.241(15.6); 1.224(15.5); 1.205(1.6); 1.186(1.2); 1.172(0.6);1.169(0.5); 0.996(15.2); 0.979(15.1); 0.965(0.8); 0.853(0.3); 0.000(1.5)26 3.18 3.08 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.345(1.9); 9.340(2.0);8.833(1.4); 8.829(1.6); 8.821(1.5); 8.817(1.6); 8.625(6.3); 8.556(0.8);8.551(1.2); 8.546(0.9); 8.536(0.9); 8.530(1.2); 8.526(0.9); 7.679(1.1);7.667(1.1); 7.660(1.1); 7.646(1.0); 7.550(1.4); 7.546(2.6); 7.542(1.7);7.525(0.7); 7.505(2.0); 7.486(2.0); 7.477(1.3); 7.473(2.2); 7.469(1.4);7.457(0.6); 7.453(0.8); 7.364(1.0); 7.360(1.5); 7.355(1.0); 7.345(0.9);7.340(1.1); 7.337(0.8); 3.329(56.9); 2.941(4.9); 2.924(5.0); 2.676(0.4);2.671(0.5); 2.667(0.4); 2.524(1.7); 2.511(32.1); 2.507(63.8);2.502(83.8); 2.498(62.6); 2.333(0.4); 2.329(0.5); 2.324(0.4);1.895(0.4); 1.878(0.9); 1.862(1.1); 1.845(0.9); 1.828(0.5); 1.234(0.5);1.020(16.0); 1.003(15.4); 0.000(8.1) 27 1.73 1.68 1H-NMR(400.0 MHz,d₆-DMSO): δ = 9.351(5.0); 9.346(5.1); 8.835(3.7); 8.831(4.0);8.823(4.0); 8.819(3.9); 8.724(0.3); 8.706(14.0); 8.561(2.1); 8.557(2.9);8.552(2.2); 8.541(2.3); 8.536(3.1); 8.532(2.2); 7.924(6.3); 7.860(2.3);7.857(1.6); 7.846(3.0); 7.842(5.0); 7.838(3.2); 7.824(2.8); 7.805(5.5);7.786(4.3); 7.784(4.2); 7.779(5.4); 7.774(3.3); 7.764(1.3); 7.760(1.8);7.755(1.0); 7.681(2.8); 7.669(2.8); 7.661(2.8); 7.649(2.6); 5.757(4.4);3.332(67.3); 2.853(0.6); 2.820(4.9); 2.814(4.8); 2.800(8.5); 2.782(0.7);2.766(0.3); 2.672(0.7); 2.507(77.9); 2.503(99.5); 2.498(76.3);2.330(0.7); 2.325(0.5); 2.160(0.9); 2.143(1.5); 2.126(1.8); 2.108(1.5);2.091(0.9); 2.075(0.3); 1.233(1.0); 1.192(0.4); 1.130(15.9);1.113(15.7); 1.094(0.8); 1.034(15.8); 1.017(16.0); 1.004(1.2);0.995(0.9); 0.977(0.3); 0.000(0.8) 28 2.47 2.43 1H-NMR(600.1 MHz,CD3CN): = 9.2734(3.7); 9.2728(3.7); 9.270(3.8); 8.751(2.8); 8.748(2.9);8.743(2.9); 8.740(2.8); 8.469(9.8); 8.403(1.8); 8.400(2.4); 8.399(2.3);8.396(1.7); 8.389(1.9); 8.387(2.4); 8.386(2.3); 8.383(1.7); 7.744(3.9);7.662(2.1); 7.650(3.1); 7.641(2.5); 7.576(2.2); 7.563(3.2); 7.550(1.3);7.534(2.3); 7.533(2.2); 7.526(2.3); 7.525(2.2); 7.521(2.3); 7.520(2.1);7.513(2.2); 7.512(2.0); 5.293(16.0); 2.957(13.9); 2.827(11.1);2.154(11.6); 1.972(12.0); 1.967(0.5); 1.959(0.6); 1.955(0.8);1.951(5.6); 1.947(10.0); 1.943(14.5); 1.938(9.7); 1.934(4.8); 0.000(6.8)32 1.91 1.92 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.303(2.1); 9.297(2.1);8.859(5.1); 8.814(1.4); 8.810(1.7); 8.802(1.5); 8.798(1.6); 8.513(0.8);8.508(1.2); 8.503(0.9); 8.493(0.9); 8.487(1.3); 8.483(0.9); 7.658(1.2);7.646(1.2); 7.638(1.1); 7.626(1.1); 7.300(1.2); 7.280(2.2); 7.260(1.4);6.987(2.0); 6.943(1.5); 6.924(1.3); 6.899(1.2); 6.894(1.1); 6.879(1.0);6.873(1.0); 5.241(6.2); 3.744(16.0); 3.332(39.1); 2.945(0.5);2.785(0.5); 2.673(0.4); 2.668(0.4); 2.508(50.3); 2.504(67.2);2.499(52.6); 2.330(0.4); 1.958(0.5); 1.233(0.5); 0.008(1.6); 0.000(42.7)34 1.09 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.324 (8.2); 9.320 (8.0); 8.828(5.9); 8.819 (5.7); 8.652 (16.0); 8.533 (4.1); 8.528 (5.4); 8.523 (3.9);8.513 (4.3); 8.508 (5.6); 8.503 (3.8); 7.673 (4.7); 7.661 (4.8); 7.653(4.6); 7.641 (4.2); 6.830 (1.0); 6.818 (1.8); 6.805 (0.9); 6.700 (2.0);6.688 (3.9); 6.676 (2.0); 6.570 (1.0); 6.558 (2.0); 6.546 (1.0); 4.914(5.2); 4.875 (10.9); 4.837 (5.5); 3.905 (7.6); 3.506 (0.4); 3.338(626.8); 3.225 (1.1); 3.062 (0.9); 2.677 (2.1); 2.672 (2.7); 2.668(2.1); 2.508 (339.6); 2.503 (425.1); 2.499 (319.3); 2.334 (1.9); 2.330(2.5); 2.325 (1.9); 1.298 (0.4); 1.258 (0.5); 1.233 (0.7); 1.145 (0.7);0.000 (37.7) 35 0.72 LC-MS: mass found [m/z] = 321.07 36 0.551H-NMR(400.0 MHz, d₆-DMSO): δ = 9.319 (4.3); 9.314 (4.3); 8.846 (14.5);8.822 (3.1); 8.813 (3.3); 8.554 (4.4); 8.542 (4.4); 8.527 (2.8); 8.522(3.4); 8.517 (2.5); 8.507 (2.8); 8.501 (3.4); 8.497 (2.4); 8.489 (0.5);8.364 (0.4); 8.357 (0.4); 7.669 (2.7); 7.657 (2.8); 7.649 (2.9); 7.637(2.6); 7.331 (6.3); 7.317 (6.1); 5.316 (16.0); 3.905 (6.2); 3.508 (0.4);3.469 (0.4); 3.349 (770.9); 2.678 (1.1); 2.673 (1.5); 2.669 (1.1); 2.526(4.9); 2.513 (93.8); 2.508 (184.1); 2.504 (238.5); 2.500 (175.4); 2.495(88.2); 2.335 (1.1); 2.331 (1.4); 2.326 (1.1); 1.234 (0.6); 0.008 (0.7);0.000 (21.0); −0.008 (0.8) 37 0.97 1.08 1H-NMR(400.0 MHz, d₆-DMSO): δ =9.295(1.6); 9.290(1.6); 8.809(6.3); 8.797(1.4); 8.793(1.4); 8.746(0.3);8.743(0.3); 8.503(0.8); 8.498(1.1); 8.493(0.9); 8.483(0.9); 8.478(1.2);8.473(0.9); 8.350(0.3); 7.772(3.5); 7.652(1.1); 7.640(1.1); 7.632(1.1);7.622(1.3); 7.603(0.3); 7.595(0.4); 7.583(0.3); 7.563(0.6); 7.554(0.3);7.506(3.6); 7.480(0.5); 7.460(0.5); 7.363(0.8); 7.325(0.5); 7.118(0.4);7.008(0.3); 5.757(1.6); 5.097(6.4); 4.268(0.7); 4.254(0.7); 4.205(0.4);4.191(0.4); 3.950(0.3); 3.788(4.5); 3.782(16.0); 3.750(0.6); 3.703(0.3);3.394(0.4); 3.328(25.5); 3.264(0.5); 2.676(0.4); 2.672(0.5); 2.667(0.4);2.542(0.4); 2.525(1.2); 2.512(29.4); 2.507(60.8); 2.503(81.9);2.498(62.0); 2.494(32.1); 2.334(0.4); 2.330(0.6); 2.325(0.4);2.287(1.3); 1.318(0.3); 1.298(1.0); 1.278(0.4); 1.259(1.3); 1.233(1.3);1.212(0.4); 1.196(0.3); 0.008(2.4); 0.000(75.0); −0.008(3.4); −0.150(0.3) 38 1.36 1.42 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.305(2.2);9.301(2.3); 8.815(1.6); 8.812(1.9); 8.798(6.3); 8.511(1.3); 8.506(1.0);8.495(1.0); 8.490(1.4); 8.486(1.1); 7.661(1.3); 7.648(1.3); 7.641(1.3);7.628(1.2); 7.454(4.1); 7.277(0.5); 5.759(0.4); 5.308(7.1); 4.489(0.4);4.476(0.4); 3.332(61.6); 2.945(0.9); 2.784(0.8); 2.672(0.9); 2.655(1.3);2.637(2.1); 2.611(16.0); 2.507(95.2); 2.503(124.7); 2.499(102.9);2.446(0.4); 2.330(0.8); 2.288(0.7); 1.958(0.8); 1.313(0.5); 0.146(0.4);0.000(71.2); −0.150 (0.4) 39 1.53 1.52 1H-NMR(601.6 MHz, CDCl₃): δ =9.341(5.1); 9.338(5.0); 8.781(3.5); 8.775(3.6); 8.426(2.9); 8.423(3.9);8.420(2.8); 8.413(3.1); 8.410(4.0); 8.407(2.8); 8.299(16.0); 7.484(3.2);7.476(3.3); 7.471(3.3); 7.463(3.1); 7.432(0.6); 7.261(86.9); 7.084(0.5);5.299(2.5); 3.958(15.5); 3.946(15.6); 3.278(0.4); 3.269(0.5);3.266(0.4); 3.257(0.4); 2.232(0.4); 2.220(0.6); 2.207(0.4); 1.637(0.4);1.558(13.5); 1.445(0.4); 1.368(0.5); 1.360(0.9); 1.355(1.3); 1.352(0.9);1.347(2.2); 1.342(2.1); 1.339(1.8); 1.334(3.5); 1.329(2.0); 1.326(2.4);1.321(2.7); 1.313(2.0); 1.309(1.8); 1.301(1.4); 1.255(7.8); 0.892(1.0);0.881(1.8); 0.869(1.1); 0.856(0.4); 0.841(0.4); 0.715(2.2); 0.707(6.7);0.705(7.1); 0.697(3.5); 0.694(7.0); 0.692(6.7); 0.684(2.5); 0.577(0.4);0.575(0.4); 0.564(0.4); 0.562(0.4); 0.491(2.4); 0.483(8.8); 0.473(8.4);0.465(2.0); 0.276(0.4); 0.267(0.5); 0.097(0.4); 0.005(2.9); 0.000(86.6);−0.006(3.2); −0.100(0.4) 40 1.70 1.69 1H-NMR(400.0 MHz, d6-DMSO): δ =9.347(5.5); 9.343(5.8); 8.838(4.1); 8.835(4.6); 8.826(4.5); 8.823(4.6);8.709(16.0); 8.692(0.3); 8.558(3.0); 8.554(4.0); 8.553(3.9); 8.549(3.2);8.538(3.3); 8.534(4.1); 8.533(4.3); 8.528(3.4); 8.319(0.3); 8.236(1.6);7.749(2.1); 7.745(2.5); 7.730(4.4); 7.726(5.0); 7.711(2.6); 7.706(2.9);7.683(4.8); 7.678(1.9); 7.670(4.7); 7.664(6.0); 7.650(5.7); 7.644(3.1);7.639(2.1); 7.630(1.9); 7.626(1.7); 7.556(3.1); 7.554(3.4); 7.532(4.4);7.528(3.8); 7.510(2.4); 7.507(2.4); 7.481(0.3); 7.470(3.3); 7.468(3.3);7.451(5.2); 7.449(5.3); 7.432(2.5); 7.429(2.5); 5.758(1.7); 4.354(0.3);4.336(0.4); 4.252(0.6); 4.234(0.6); 3.364(1.0); 2.678(0.5); 2.673(0.7);2.669(0.5); 2.526(1.6); 2.522(2.4); 2.513(34.4); 2.508(71.9);2.504(96.4); 2.499(71.1); 2.495(35.5); 2.335(0.6); 2.331(0.8);2.326(0.6); 2.287(0.4); 2.077(2.4); 1.342(0.5); 1.335(0.6); 1.318(1.0);1.300(0.8); 1.296(1.0); 1.278(1.5); 1.260(0.9); 1.232(0.7); 0.146(0.9);0.008(7.0); 0.000(192.4); −0.009(8.3); −0.150(0.9) 41 2.33 2.341H-NMR(400.0 MHz, d6-DMSO): δ = 9.344(5.7); 9.339(6.0); 8.833(4.1);8.829(4.6); 8.821(4.4); 8.817(4.6); 8.627(16.0); 8.554(2.3); 8.549(3.4);8.544(2.5); 8.534(2.5); 8.529(3.6); 8.524(2.5); 7.678(3.2); 7.666(3.2);7.658(3.2); 7.646(3.0); 7.576(3.2); 7.556(6.7); 7.535(4.2); 7.372(3.8);7.366(6.9); 7.361(4.9); 7.283(4.3); 7.278(4.5); 7.275(4.6); 7.266(4.6);7.261(3.9); 7.254(3.7); 7.248(3.1); 5.754(0.8); 4.878(2.5); 4.856(8.1);4.834(8.5); 4.812(2.9); 4.738(0.4); 3.319(61.3); 2.676(0.6); 2.671(0.8);2.667(0.7); 2.506(96.9); 2.502(128.4); 2.498(98.2); 2.333(0.6);2.329(0.8); 2.324(0.6); 1.234(1.8); 1.187(0.5); 0.008(0.6); 0.000(16.4)42 1.63 1.72 1H-NMR(400.0 MHz, d6-DMSO): δ = 9.350(1.3); 9.345(1.3);8.835(0.9); 8.831(1.0); 8.823(1.0); 8.819(1.0); 8.714(3.3); 8.560(0.5);8.556(0.7); 8.551(0.5); 8.540(0.6); 8.535(0.8); 8.531(0.5); 8.055(1.6);7.967(0.6); 7.962(0.4); 7.948(1.0); 7.944(0.7); 7.929(0.5); 7.925(0.4);7.909(1.4); 7.894(1.3); 7.875(1.1); 7.856(0.4); 7.680(0.7); 7.668(0.7);7.660(0.7); 7.648(0.7); 3.320(7.9); 2.681(16.0); 2.507(13.0);2.502(16.4); 2.498(12.5); 0.000(16.1) 43 2.05 2.06 1H-NMR(400.0 MHz,d6-DMSO): δ = 9.343(2.6); 8.829(1.8); 8.820(1.9); 8.635(3.7);8.549(1.5); 8.530(1.6); 7.666(6.6); 7.647(6.5); 7.625(2.2); 7.459(0.4);7.412(0.5); 7.390(0.6); 7.364(0.7); 7.333(0.9); 7.267(0.4); 7.245(0.3);7.181(1.3); 7.115(0.4); 3.318(83.2); 2.671(2.4); 2.501(395.6);2.327(3.0); 2.286(1.2); 2.180(0.5); 1.988(0.4); 1.386(2.2); 1.335(12.4);1.298(9.2); 1.249(16.0); 1.235(16.0); 1.188(3.6); 1.105(1.7);0.852(4.1); 0.834(3.9); 0.146(0.4); 0.000(59.8); −0.151(0.4) 44 2.913.00 1H-NMR(400.0 MHz, d6-DMSO): δ = 9.345(7.4); 9.340(7.7); 8.836(5.3);8.834(5.7); 8.825(5.5); 8.822(5.6); 8.700(16.0); 8.550(4.4); 8.534(3.2);8.530(4.5); 7.753(4.1); 7.747(4.7); 7.736(4.3); 7.730(4.5); 7.681(4.1);7.669(4.1); 7.661(4.1); 7.649(3.9); 7.601(1.9); 7.595(2.1); 7.589(2.3);7.579(3.1); 7.573(3.1); 7.568(3.1); 7.562(2.6); 7.490(4.6); 7.467(6.6);7.444(3.2); 3.312(33.5); 2.988(15.3); 2.970(15.6); 2.672(0.7);2.502(104.5); 2.329(0.6); 2.074(2.1); 1.234(0.4); 1.085(0.6);1.078(1.0); 1.066(1.9); 1.059(1.8); 1.047(2.9); 1.035(1.9); 1.029(2.1);1.016(1.1); 1.010(0.7); 0.998(0.3); 0.567(2.3); 0.556(7.5); 0.552(8.2);0.536(7.6); 0.532(7.5); 0.522(2.6); 0.282(2.7); 0.269(9.5); 0.256(9.5);0.245(2.2); 0.000(8.6) 45 1.63 1.66 1H-NMR(400.0 MHz, d6-DMSO): δ =9.354(9.8); 9.353(9.9); 9.349(9.7); 8.841(7.9); 8.837(8.0); 8.829(8.1);8.825(7.7); 8.759(8.5); 8.753(16.0); 8.564(4.8); 8.560(6.0); 8.554(4.1);8.544(5.1); 8.540(6.0); 8.538(5.7); 8.534(3.9); 8.369(1.6); 8.363(1.7);8.352(1.6); 8.346(1.6); 8.318(1.2); 8.185(0.9); 8.179(0.9); 8.173(1.1);8.167(1.1); 8.163(1.1); 8.157(1.1); 8.152(1.1); 8.146(0.9); 8.087(4.6);8.082(5.1); 8.070(4.8); 8.065(4.8); 7.965(2.7); 7.960(2.7); 7.954(3.4);7.948(3.1); 7.943(3.4); 7.938(3.3); 7.932(3.3); 7.927(2.7); 7.872(1.0);7.869(1.3); 7.862(1.7); 7.851(0.7); 7.840(2.5); 7.817(1.4); 7.785(5.2);7.762(7.2); 7.740(4.3); 7.687(6.0); 7.675(5.9); 7.667(5.8); 7.655(5.5);7.589(0.4); 7.571(0.6); 5.758(8.2); 5.599(0.5); 4.153(0.4); 4.142(0.5);4.129(0.4); 3.852(0.4); 3.601(0.5); 3.589(0.5); 3.577(0.4); 3.519(1.8);3.506(0.8); 3.378(4.0); 3.360(4.6); 3.329(329.8); 3.279(0.4);3.273(0.5); 2.977(0.4); 2.927(7.4); 2.909(7.4); 2.891(3.0); 2.844(0.4);2.820(8.6); 2.748(0.5); 2.732(1.9); 2.676(2.3); 2.672(3.1); 2.667(2.4);2.650(0.3); 2.621(0.4); 2.595(2.0); 2.584(0.8); 2.525(12.9);2.511(184.2); 2.507(356.1); 2.503(459.1); 2.498(337.4); 2.494(171.5);2.334(2.2); 2.329(2.9); 2.325(2.2); 2.087(6.4); 1.492(0.4); 1.474(0.5);1.454(0.4); 1.291(0.4); 1.274(0.6); 1.259(0.9); 1.234(2.5); 1.187(0.4);0.996(0.9); 0.984(1.8); 0.977(1.8); 0.965(2.6); 0.953(1.9); 0.946(2.0);0.934(1.4); 0.921(0.9); 0.915(1.0); 0.902(1.1); 0.889(0.8); 0.883(0.9);0.870(0.8); 0.862(1.0); 0.852(0.9); 0.844(1.8); 0.825(1.8); 0.806(0.7);0.608(0.5); 0.585(2.5); 0.574(8.6); 0.565(4.7); 0.554(8.4); 0.545(2.8);0.531(0.7); 0.522(1.0); 0.504(2.6); 0.484(2.4); 0.342(1.8); 0.336(1.9);0.322(4.0); 0.311(3.7); 0.296(0.9); 0.284(0.9); 0.270(3.7); 0.258(4.0);0.245(2.0); 0.238(1.7); 0.227(0.8); 0.146(5.9); 0.137(2.5); 0.053(0.3);0.008(34.5); 0.000(766.5); −0.008 (43.1); −0.064(0.6); −0.079(0.4);−0.099(0.3); −0.150 (3.6) 46 2.60 2.56 1H-NMR(400.0 MHz, d6-DMSO): δ =9.351(5.7); 9.347(5.7); 8.841(4.5); 8.837(5.0); 8.829(4.8); 8.825(4.9);8.710(16.0); 8.563(2.6); 8.558(3.5); 8.553(2.7); 8.543(2.9); 8.537(3.6);8.533(2.7); 8.317(1.0); 7.948(3.6); 7.942(4.0); 7.931(3.7); 7.925(3.8);7.791(1.9); 7.785(2.0); 7.780(2.2); 7.774(2.1); 7.770(2.3); 7.763(2.4);7.758(2.4); 7.752(2.0); 7.685(3.4); 7.672(3.3); 7.666(3.3); 7.654(3.1);7.652(3.1); 7.571(3.9); 7.548(5.4); 7.525(3.2); 4.139(2.5); 4.114(7.7);4.088(8.1); 4.062(2.7); 3.330(493.3); 3.288(0.4); 2.676(2.0);2.671(2.7); 2.667(2.0); 2.525(7.4); 2.511(147.5); 2.507(299.9);2.502(398.3); 2.498(297.0); 2.494(151.2); 2.457(1.0); 2.437(0.6);2.334(2.0); 2.329(2.7); 2.325(2.0); 2.075(3.9); 0.146(0.9); 0.008(6.8);0.000(200.5); −0.008(8.5); −0.150(0.9) 47 2.73 2.75 1H-NMR(400.0 MHz,d6-DMSO): δ = 10.481(0.3); 9.349(3.0); 9.344(3.0); 8.834(2.4);8.830(2.6); 8.822(2.5); 8.818(2.6); 8.612(10.2); 8.559(1.4); 8.554(1.8);8.549(1.4); 8.539(1.5); 8.534(2.0); 8.529(1.5); 8.435(0.6); 7.787(0.4);7.769(3.7); 7.764(3.7); 7.679(1.8); 7.667(1.8); 7.659(1.8); 7.647(1.7);7.472(2.0); 7.451(3.9); 7.415(2.9); 7.410(2.8); 7.395(1.5); 7.390(1.5);5.757(0.9); 4.118(1.2); 4.092(3.8); 4.066(4.0); 4.040(1.4); 3.880(0.4);3.865(0.4); 3.854(0.4); 3.848(0.4); 3.328(110.4); 2.676(0.7);2.671(0.9); 2.667(0.7); 2.525(2.5); 2.511(52.6); 2.507(105.2);2.502(138.7); 2.498(103.1); 2.493(51.6); 2.427(16.0); 2.358(1.6);2.334(0.7); 2.329(1.0); 2.324(0.8); 1.233(0.5); 1.201(0.4); 1.184(0.9);1.166(0.4); 0.146(0.9); 0.008(7.4); 0.000(188.5); −0.009(7.9);−0.150(0.9) 48 1.86 1.85 1H-NMR(400.0 MHz, d6-DMSO): δ = 9.350(3.3);9.345(3.3); 8.834(2.3); 8.830(2.5); 8.822(2.4); 8.818(2.4); 8.689(8.7);8.559(1.4); 8.555(1.9); 8.550(1.4); 8.539(1.5); 8.534(2.0); 8.530(1.4);8.145(1.0); 8.046(4.0); 8.041(4.2); 7.895(0.7); 7.891(0.6); 7.878(0.4);7.758(1.9); 7.753(1.8); 7.738(2.4); 7.733(2.4); 7.679(1.9); 7.668(2.0);7.660(1.8); 7.648(1.7); 7.594(3.3); 7.573(2.6); 7.531(0.4); 4.272(0.9);4.263(0.5); 4.253(0.7); 4.245(1.1); 4.235(1.8); 4.217(0.6); 4.208(1.3);4.181(0.4); 4.123(0.4); 4.096(1.2); 4.087(0.4); 4.069(1.4); 4.059(1.0);4.042(0.5); 4.032(0.9); 3.320(6.0); 2.996(0.5); 2.671(0.5); 2.667(0.4);2.506(55.7); 2.502(71.4); 2.498(55.1); 2.477(16.0); 2.329(0.5);1.296(0.5); 1.278(1.1); 1.260(0.5); 0.000(2.1) 49 3.04 2.98 1H-NMR(400.0MHz, d₆-DMSO): δ = 9.347(2.9); 9.342(3.0); 8.838(2.3); 8.834(2.4);8.826(2.4); 8.822(2.5); 8.558(1.3); 8.554(1.9); 8.548(1.4); ,536(10.2);8.528(1.5); 8.317(0.8); 7.924(0.4); 7.683(1.9); 7.675(6.4); 7.665(2.0);7.651(1.5); 7.360(4.7); 6.025(1.0); 4.055(0.6); 4.038(2.6); 4.020(2.4);4.014(3.6); 4.002(0.9); 3.988(3.6); 3.962(1.3); 3.855(0.8); 3.837(0.8);3.392(0.3); 3.374(0.5); 3.332(421.8); 2.676(1.7); 2.671(2.3);2.667(1.7); 2.525(5.6); 2.511(131.6); 2.507(269.9); 2.502(357.0);2.498(264.5); 2.494(133.5); 2.407(15.0); 2.365(0.4); 2.334(1.8);2.329(2.4); 2.325(1.8); 2.078(16.0); 1.989(7.6); 1.890(0.3); 1.398(1.9);1.235(0.6); 1.193(2.1); 1.175(4.1); 1.157(2.1); 1.100(0.8); 1.083(1.5);1.065(0.8); 0.146(0.5); 0.008(3.7); 0.000(116.2); −0.008(4.9);−0.150(0.5) 50 2.06 2.01 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.351(4.6);9.346(4.6); 8.839(3.4); 8.835(3.7); 8.827(3.6); 8.823(3.7); 8.591(14.3);8.561(1.9); 8.556(2.7); 8.551(1.9); 8.541(2.0); 8.536(2.8); 8.531(1.9);8.317(1.3); 7.937(6.3); 7.928(4.2); 7.685(2.6); 7.673(2.6); 7.667(2.5);7.653(2.4); 7.496(3.0); 7.470(4.4); 4.323(0.5); 4.295(0.6); 4.286(0.7);4.259(0.7); 4.178(0.6); 4.171(0.6); 4.151(1.8); 4.144(1.8); 4.124(1.8);4.117(1.8); 4.097(0.7); 4.090(0.6); 4.055(0.4); 4.037(1.0); 4.020(1.0);4.002(0.4); 3.977(0.7); 3.951(0.8); 3.940(0.7); 3.924(0.3); 3.914(0.7);3.372(0.9); 3.332(833.0); 2.676(2.9); 2.671(3.9); 2.667(2.9);2.525(9.7); 2.507(449.3); 2.502(587.2); 2.498(437.0); 2.451(12.1);2.446(16.0); 2.408(0.8); 2.353(0.6); 2.334(3.2); 2.329(4.0); 2.325(3.0);2.279(0.4); 2.258(0.5); 2.188(15.9); 2.182(12.0); 1.989(4.2);1.193(1.1); 1.175(2.3); 1.157(1.1); 0.146(0.8); 0.008(6.5);0.000(190.8); −0.008(8.2); −0.150(0.9) 51 3.25 3.17 1H-NMR(400.0 MHz,d6-DMSO): δ = 9.354(5.1); 9.348(5.2); 8.844(3.9); 8.840(4.4);8.832(4.1); 8.828(4.4); 8.658(16.0); 8.565(2.1); 8.561(3.0); 8.556(2.3);8.546(2.3); 8.540(3.2); 8.536(2.3); 8.138(10.9); 8.091(13.9);8.003(0.3); 7.812(0.5); 7.687(2.9); 7.675(2.9); 7.667(2.9); 7.655(2.8);5.757(3.1); 4.262(0.4); 4.248(0.9); 4.238(1.2); 4.223(2.7); 4.213(2.8);4.198(2.9); 4.188(2.8); 4.173(1.3); 4.163(1.0); 4.149(0.4); 3.340(73.8);2.676(0.9); 2.671(1.2); 2.667(0.9); 2.524(3.2); 2.511(67.2);2.507(136.2); 2.502(181.2); 2.498(135.3); 2.493(68.1); 2.333(0.8);2.329(1.2); 2.324(0.9); 2.287(0.6); 1.234(0.3); 0.000(7.9) 52 1.57 1.551H-NMR(400.0 MHz, d6-DMSO): δ = 9.342(2.1); 9.337(2.1); 8.831(1.5);8.828(1.6); 8.819(1.6); 8.816(1.6); 8.620(5.9); 8.552(0.9); 8.547(1.3);8.542(0.9); 8.532(1.0); 8.527(1.3); 8.522(0.9); 7.677(1.2); 7.664(1.2);7.657(1.3); 7.645(1.2); 7.601(2.8); 7.543(0.5); 7.539(0.5); 7.525(4.0);7.509(2.3); 7.489(0.8); 7.397(1.0); 7.392(1.6); 7.386(1.0); 7.380(0.9);7.375(1.3); 7.370(0.8); 5.754(9.1); 4.101(8.1); 3.986(0.9); 3.977(0.6);3.962(0.4); 3.320(15.8); 3.053(16.0); 3.044(2.3); 2.849(15.1);2.507(32.7); 2.502(41.4); 2.498(30.9); 1.187(0.4); 0.000(3.5) 53 0.911.08 1H-NMR(400.0 MHz, d6-DMSO): δ = 9.349(2.0); 8.833(1.5); 8.823(1.5);8.697(5.9); 8.556(1.4); 8.552(1.1); 8.541(1.1); 8.536(1.5); 8.140(1.0);7.968(3.1); 7.904(0.8); 7.900(0.8); 7.893(1.7); 7.886(1.2); 7.882(1.3);7.878(1.2); 7.820(0.4); 7.799(3.8); 7.788(3.6); 7.682(1.3); 7.669(1.3);7.662(1.4); 7.649(1.2); 5.754(3.5); 4.219(0.7); 4.182(3.7); 4.166(3.5);4.129(0.8); 4.100(0.4); 4.090(0.3); 3.318(8.9); 3.053(0.6); 2.934(16.0);2.915(1.8); 2.858(14.1); 2.844(2.3); 2.671(0.7); 2.505(83.9);2.502(106.8); 2.498(84.9); 2.328(0.7); 2.074(0.6); 0.000(3.2) 54 1.901.91 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.347(2.8); 9.342(2.6); 8.837(2.0);8.825(2.0); 8.668(5.5); 8.552(1.6); 8.532(1.6); 8.141(0.9); 7.718(2.4);7.700(2.4); 7.682(1.5); 7.669(1.5); 7.662(1.4); 7.649(1.3); 7.448(2.1);7.422(2.1); 5.754(0.6); 4.011(8.8); 3.320(45.4); 3.027(16.0);2.891(0.5); 2.832(14.9); 2.731(0.5); 2.670(0.6); 2.502(95.0);2.406(12.3); 2.328(0.6); 0.000(4.0) 55 1.38 1.38 1H-NMR(400.0 MHz,d₆-DMSO): δ = 9.350(3.2); 9.345(3.1); 8.838(2.2); 8.835(2.3);8.826(2.3); 8.823(2.3); 8.722(6.2); 8.556(1.8); 8.540(1.4); 8.535(1.9);8.531(1.3); 8.139(4.6); 8.119(2.9); 7.685(1.7); 7.672(1.7); 7.665(1.7);7.653(1.5); 7.568(2.4); 7.541(2.4); 4.185(1.3); 4.148(2.5); 4.086(1.2);4.047(0.6); 3.340(160.4); 2.955(16.0); 2.863(15.8); 2.672(0.6);2.507(78.3); 2.503(97.2); 2.473(15.1); 2.330(0.6); 0.000(3.2) 56 3.253.00 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.333(2.4); 9.328(2.4); 8.834(1.8);8.830(2.0); 8.822(1.9); 8.818(2.0); 8.535(1.1); 8.531(1.4); 8.526(1.1);8.515(1.2); 8.510(1.5); 8.506(1.1); 7.939(2.4); 7.920(2.4); 7.680(1.4);7.668(1.4); 7.661(1.4); 7.648(1.3); 7.541(2.1); 7.515(2.1); 4.085(0.5);4.071(0.5); 4.060(0.6); 4.046(1.3); 4.037(0.6); 4.021(1.3); 4.012(1.3);3.995(0.7); 3.986(1.3); 3.972(0.5); 3.960(0.5); 3.946(0.5); 3.329(49.4);2.676(0.4); 2.672(0.5); 2.668(0.4); 2.525(1.3); 2.512(29.6);2.507(59.8); 2.503(79.0); 2.498(58.4); 2.494(29.1); 2.469(13.3);2.443(0.6); 2.417(0.6); 2.339(0.3); 2.334(0.5); 2.329(0.6); 2.325(0.5);2.302(0.4); 2.281(16.0); 2.076(1.0); 0.008(1.9); 0.000(57.6);−0.009(2.3) 57 2.25 2.05 1H-NMR(601.6 MHz, CDCl₃): δ = 9.363(2.0);8.807(1.5); 8.469(0.8); 8.466(1.1); 8.463(0.8); 8.452(1.9); 8.441(0.9);8.438(1.1); 8.435(0.8); 8.065(1.7); 8.029(1.8); 8.017(1.8); 8.003(1.8);7.991(1.8); 7.979(1.0); 7.966(1.1); 7.556(0.7); 7.554(0.7); 7.542(0.9);7.541(0.9); 7.526(0.9); 7.519(1.3); 7.513(1.7); 7.507(1.3); 7.500(0.9);7.415(1.0); 7.402(1.7); 7.389(0.8); 7.304(1.8); 7.302(1.9); 7.288(1.9);7.286(1.8); 7.272(7.2); 5.302(6.3); 3.617(0.5); 3.609(0.4); 3.601(0.6);3.593(1.0); 3.576(1.1); 3.563(1.1); 3.555(0.3); 3.547(3.0); 3.539(0.6);3.530(3.1); 3.523(0.8); 3.514(1.2); 3.506(0.7); 2.590(0.5); 2.517(16.0);2.501(0.6); 2.493(0.4); 2.484(0.3); 2.418(0.7); 2.408(12.8); 2.395(0.6);2.386(12.7); 2.378(1.1); 2.369(0.4); 2.356(0.5); 2.352(0.4); 2.344(0.4);2.332(0.4); 1.335(0.5); 1.329(0.3); 1.306(0.6); 1.295(0.9); 1.286(1.3);1.283(1.3); 1.271(1.3); 1.255(6.2); 1.232(0.7); 1.221(0.5); 1.212(0.5);0.891(0.8); 0.880(1.4); 0.868(1.0); 0.856(0.5); 0.843(0.9); 0.841(0.9);0.834(0.9); 0.005(0.5); 0.000(14.7); −0.006(0.7) 58 3.45 3.321H-NMR(400.0 MHz, DMSO): δ = 9.430(10.3); 9.425(10.4); 8.891(8.1);8.887(8.8); 8.879(8.5); 8.875(8.7); 8.651(4.7); 8.646(6.4); 8.641(4.7);8.631(5.1); 8.625(6.5); 8.621(4.7); 8.317(0.4); 8.260(1.0); 8.242(1.1);7.992(9.9); 7.973(9.9); 7.729(6.1); 7.717(6.0); 7.709(6.0); 7.697(6.2);7.673(0.9); 7.583(8.6); 7.556(8.5); 5.758(16.0); 4.361(0.7); 4.351(0.4);4.344(0.4); 4.324(0.4); 4.086(0.4); 4.059(0.4); 4.049(0.4); 4.018(4.1);3.993(12.7); 3.967(13.1); 3.941(4.5); 3.331(218.6); 2.677(1.1);2.672(1.5); 2.668(1.1); 2.512(92.5); 2.508(154.3); 2.503(197.3);2.499(145.6); 2.495(73.3); 2.374(0.4); 2.353(0.4); 2.334(1.0);2.330(1.3); 2.326(1.0); 1.343(0.4); 1.326(0.8); 1.308(0.4); 0.146(0.4);0.008(3.0); 0.000(84.9); −0.008(3.4); −0.150 (0.4) 59 2.40 2.351H-NMR(400.0 MHz, DMSO): δ = 9.432(5.9); 9.428(6.0); 8.891(4.5);8.887(4.8); 8.879(4.8); 8.875(4.8); 8.652(2.6); 8.648(3.5); 8.642(2.6);8.632(2.8); 8.626(3.7); 8.622(2.7); 8.260(5.9); 8.241(6.0); 7.729(3.3);7.717(3.3); 7.709(3.5); 7.699(7.6); 7.673(4.8); 5.758(16.0); 4.415(0.5);4.388(1.7); 4.378(0.8); 4.360(2.0); 4.351(2.3); 4.333(0.8); 4.323(2.3);4.296(0.7); 4.112(0.6); 4.085(2.0); 4.075(0.7); 4.058(2.3); 4.048(1.9);4.031(0.9); 4.021(1.8); 3.994(0.6); 3.331(101.6); 2.676(0.7);2.672(1.0); 2.668(0.8); 2.507(117.2); 2.503(134.4); 2.498(99.6);2.334(0.6); 2.330(0.9); 2.325(0.7); 1.233(0.7); 0.008(1.1); 0.000(27.5)60 2.41 2.45 1H-NMR(400.0 MHz, d6-DMSO): δ = 9.339(7.0); 8.827(5.1);8.818(4.9); 8.618(9.6); 8.546(4.0); 8.527(4.0); 8.312(0.4); 7.676(3.3);7.661(3.9); 7.646(2.9); 7.529(5.3); 7.509(15.6); 7.494(14.9);7.475(4.6); 3.643(0.5); 3.637(0.5); 3.606(0.5); 3.586(0.6);3.331(671.5); 3.145(0.9); 3.109(3.6); 3.091(8.5); 3.073(8.4);3.055(3.4); 3.009(0.5); 2.987(0.4); 2.974(0.3); 2.959(0.3); 2.937(0.3);2.919(0.4); 2.897(0.4); 2.885(0.3); 2.803(0.4); 2.671(3.3);2.502(411.9); 2.395(1.4); 2.330(3.0); 2.243(0.3); 2.073(0.6);1.318(8.9); 1.300(16.0); 1.282(8.2); 1.235(0.6); 0.146(0.7);0.000(103.8); −0.073 (0.5); −0.141(0.3); −0.150(0.7) 61 1.10 1.221H-NMR(400.0 MHz, d6-DMSO): δ = 9.349(4.7); 9.344(4.8); 8.835(3.5);8.831(3.6); 8.823(3.7); 8.819(3.5); 8.683(11.9); 8.558(2.0); 8.554(2.8);8.548(1.9); 8.538(2.2); 8.533(2.8); 8.528(1.9); 8.313(0.4); 7.870(4.9);7.849(12.5); 7.822(12.3); 7.801(4.7); 7.681(2.6); 7.669(2.6);7.661(2.6); 7.649(2.4); 5.753(3.4); 3.317(42.6); 3.178(0.5); 3.159(1.7);3.141(2.1); 3.125(2.5); 3.107(2.2); 3.089(0.7); 2.898(0.6); 2.879(2.1);2.861(2.5); 2.845(2.1); 2.827(1.8); 2.809(0.5); 2.671(0.9);2.506(103.2); 2.502(129.1); 2.498(96.5); 2.333(0.6); 2.329(0.8);1.235(0.7); 1.113(7.6); 1.094(16.0); 1.076(7.2); 0.146(1.0); 0.033(0.4);0.000(200.8); −0.150 (1.0) 62 2.71 2.69 1H-NMR(400.0 MHz, d₆-DMSO): δ =9.954(1.2); 9.347(5.1); 9.343(5.1); 9.341(5.2); 9.106(0.9); 9.100(0.9);8.835(3.9); 8.831(4.4); 8.823(4.0); 8.819(4.4); 8.744(0.7); 8.740(0.8);8.732(0.8); 8.728(0.8); 8.701(16.0); 8.636(1.4); 8.558(2.1); 8.552(3.1);8.548(2.5); 8.538(2.3); 8.532(3.3); 8.528(2.5); 8.280(0.4); 8.275(0.5);8.271(0.4); 8.260(0.4); 8.255(0.6); 8.251(0.4); 7.969(7.3); 7.948(9.3);7.881(1.5); 7.859(2.0); 7.806(1.5); 7.799(11.4); 7.795(3.7); 7.783(3.0);7.778(9.2); 7.772(1.0); 7.688(0.6); 7.679(4.0); 7.667(4.3); 7.660(3.6);7.647(4.4); 7.625(0.4); 7.612(0.5); 7.600(0.5); 7.592(0.5); 7.579(0.5);7.333(1.3); 3.324(74.8); 2.676(0.7); 2.671(0.9); 2.667(0.7); 2.524(2.5);2.511(45.7); 2.507(92.5); 2.502(124.5); 2.498(94.2); 2.493(47.7);2.333(0.5); 2.329(0.8); 2.325(0.6); 1.298(0.5); 1.259(0.7); 1.233(1.0);0.000(1.1) 63 2.03 1.99 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.344(0.4);8.925(9.0); 8.748(0.7); 8.714(16.0); 8.649(1.1); 8.542(0.3); 8.462(5.6);8.446(5.9); 8.317(1.5); 8.137(0.4); 8.117(0.7); 8.081(5.4); 8.061(5.8);7.970(10.5); 7.950(13.1); 7.793(14.1); 7.772(11.5); 7.689(0.8);7.666(5.7); 7.647(6.7); 7.629(4.4); 5.757(7.6); 3.507(0.3); 3.487(0.3);3.447(0.4); 3.439(0.4); 3.409(0.5); 3.326(536.7); 3.245(0.3);2.840(0.4); 2.820(0.4); 2.805(0.4); 2.765(0.4); 2.671(8.5); 2.622(1.1);2.618(1.1); 2.502(1215.9); 2.329(7.9); 2.184(0.3); 1.355(0.6);1.299(1.8); 1.259(2.9); 1.235(7.6); 1.166(0.5); 1.149(1.1); 1.066(0.4);0.854(1.6); 0.843(1.0); 0.834(1.1); 0.814(0.7); 0.784(0.5); 0.146(5.7);0.083(0.5); 0.000(1101.9); −0.150(5.9) 64 2.91 2.89 1H-NMR(400.0 MHz,d6-DMSO): δ = 9.343(2.9); 9.338(3.0); 8.837(2.1); 8.833(2.4);8.825(2.3); 8.821(2.4); 8.623(8.0); 8.552(1.2); 8.548(1.7); 8.543(1.3);8.532(1.3); 8.527(1.8); 8.523(1.3); 7.871(3.3); 7.793(1.4); 7.772(1.9);7.769(1.9); 7.691(4.1); 7.683(1.9); 7.670(4.3); 7.663(1.8); 7.650(1.6);5.751(1.5); 3.310(93.8); 2.675(0.6); 2.670(0.8); 2.666(0.6); 2.523(2.1);2.506(94.0); 2.501(124.8); 2.497(95.6); 2.328(0.8); 2.323(0.6);2.200(16.0); 1.235(0.4); 0.008(0.4); 0.000(12.5) 65 1.70 1.701H-NMR(400.0 MHz, d6-DMSO): δ = 10.654(0.5); 10.355(0.5); 9.356(2.4);9.351(2.4); 9.213(0.4); 8.839(2.0); 8.835(2.0); 8.827(1.9); 8.823(1.7);8.775(0.4); 8.718(7.1); 8.560(1.4); 8.557(1.3); 8.546(1.4); 8.542(1.6);8.466(0.9); 8.383(0.5); 8.362(0.6); 8.337(1.0); 8.314(5.1); 8.241(2.4);8.220(2.6); 8.143(2.9); 8.138(2.9); 8.110(0.4); 7.994(0.4); 7.973(0.4);7.940(0.9); 7.910(5.0); 7.848(0.7); 7.837(0.5); 7.794(1.6); 7.715(0.6);7.685(1.4); 7.673(1.7); 7.667(1.6); 7.651(2.4); 7.645(2.1); 7.629(2.0);7.624(2.0); 7.593(0.5); 7.530(0.4); 7.520(0.6); 7.516(0.6); 7.494(0.6);5.924(0.4); 5.754(1.3); 5.584(0.4); 4.637(0.4); 4.306(0.4); 4.273(0.5);4.186(0.4); 4.151(0.4); 4.130(0.4); 4.096(0.4); 4.055(0.4); 4.039(0.5);4.021(0.5); 3.986(0.5); 3.967(0.6); 3.941(0.4); 3.921(0.5); 3.905(0.6);3.884(0.6); 3.868(0.7); 3.851(0.5); 3.838(0.5); 3.823(0.5); 3.765(0.5);3.692(0.6); 3.637(0.6); 3.608(0.6); 3.585(0.7); 3.573(0.7); 3.544(0.7);3.530(0.7); 3.509(0.9); 3.470(1.0); 3.452(1.0); 3.438(1.0); 3.398(1.3);3.392(1.4); 3.378(1.8); 3.317(1231.0); 3.277(1.8); 3.265(2.1);3.259(1.7); 3.254(1.7); 3.217(1.2); 3.189(1.1); 3.174(1.2); 3.147(1.3);3.123(1.4); 3.095(2.1); 3.071(2.2); 3.041(1.8); 3.002(2.0); 2.979(1.8);2.937(1.6); 2.916(0.8); 2.902(0.7); 2.889(0.8); 2.861(0.9); 2.830(0.9);2.812(1.0); 2.775(1.2); 2.710(1.6); 2.694(2.0); 2.675(12.0);2.670(16.0); 2.666(12.5); 2.561(4.8); 2.557(5.4); 2.523(51.5);2.510(893.1); 2.506(1772.8); 2.501(2326.4); 2.497(1726.9); 2.332(9.4);2.328(13.4); 2.324(9.8); 1.352(0.6); 1.336(0.7); 1.300(0.5); 1.235(6.1);1.213(1.1); 1.194(1.3); 1.176(1.0); 1.158(0.7); 0.854(1.1); 0.837(0.7);0.214(0.4); 0.196(0.4); 0.146(13.9); 0.121(0.7); 0.112(0.7); 0.104(0.8);0.091(0.7); 0.082(1.1); 0.074(1.0); 0.061(1.2); 0.056(1.0);0.008(120.2); 0.000(2914.5); −0.008 (142.9); −0.052(1.8); −0.058(0.9);−0.063(0.7); −0.068 (0.7); −0.150(13.4) 66 2.20 2.21 1H-NMR(400.0 MHz,d6-DMSO): δ = 9.340(4.1); 9.334(4.3); 8.836(2.9); 8.833(3.2);8.825(3.0); 8.821(3.2); 8.548(1.6); 8.544(2.5); 8.539(1.8); 8.525(12.5);7.682(2.3); 7.670(2.3); 7.661(2.7); 7.656(2.6); 7.650(2.8); 7.638(3.8);7.635(3.5); 7.599(2.2); 7.585(4.8); 7.566(4.6); 7.459(2.0); 7.456(2.1);7.437(3.1); 7.421(1.2); 7.418(1.3); 4.039(0.5); 4.021(0.5); 3.321(22.4);2.983(1.3); 2.979(1.6); 2.964(4.1); 2.961(4.4); 2.946(4.3); 2.943(4.4);2.928(1.6); 2.671(0.3); 2.507(39.0); 2.503(51.4); 2.499(39.7);2.330(0.3); 1.989(1.9); 1.187(7.9); 1.175(1.7); 1.168(16.0); 1.158(1.1);1.150(7.6); 0.000(1.1) 67 1.28 1.29 1H-NMR(400.0 MHz, d6-DMSO): δ =9.347(8.0); 9.342(8.3); 8.839(6.5); 8.832(13.6); 8.734(8.2); 8.553(4.6);8.533(4.8); 8.315(0.3); 8.010(3.0); 7.991(3.8); 7.974(2.1); 7.955(2.9);7.883(2.4); 7.864(5.3); 7.845(3.6); 7.834(1.8); 7.818(4.0); 7.816(4.1);7.797(4.2); 7.781(1.6); 7.712(7.0); 7.688(6.1); 7.675(4.2); 7.667(4.2);7.655(3.9); 4.356(0.5); 4.343(0.9); 4.331(0.5); 3.456(0.9); 3.443(0.9);3.439(1.0); 3.426(0.9); 3.409(0.3); 3.319(49.2); 2.979(0.5); 2.961(1.6);2.943(2.1); 2.927(2.4); 2.920(1.6); 2.908(2.3); 2.902(1.7); 2.886(2.0);2.867(1.6); 2.849(0.5); 2.700(0.6); 2.690(0.8); 2.682(2.1); 2.672(3.4);2.664(2.7); 2.654(2.7); 2.648(2.0); 2.638(2.3); 2.630(1.6); 2.620(1.8);2.611(0.7); 2.602(0.7); 2.541(1.1); 2.502(179.7); 2.329(1.0);1.077(7.4); 1.059(16.0); 1.040(8.1); 1.026(5.7); 1.007(11.5);0.989(5.3); 0.146(1.0); 0.027(0.5); 0.000(183.4); −0.150(1.0) 68 2.342.29 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.348(4.6); 9.344(4.6); 8.841(3.7);8.837(4.0); 8.829(4.0); 8.825(4.0); 8.558(2.5); 8.551(16.0); 8.539(2.6);8.533(3.3); 8.529(2.4); 7.918(3.2); 7.915(3.1); 7.899(4.0); 7.688(2.9);7.686(2.8); 7.676(2.9); 7.674(2.9); 7.667(5.2); 7.663(4.0); 7.654(4.6);7.648(3.9); 7.645(5.9); 7.639(5.5); 7.635(3.0); 7.620(3.2); 7.616(2.2);7.598(3.4); 7.595(3.5); 7.579(3.1); 7.576(3.5); 7.561(1.3); 7.557(1.2);5.757(3.6); 4.056(0.6); 4.038(1.0); 4.031(1.1); 4.020(1.3); 4.017(1.0);4.006(1.3); 3.992(2.6); 3.980(0.7); 3.967(3.0); 3.944(2.9); 3.930(0.6);3.918(2.8); 3.905(1.2); 3.892(1.0); 3.878(1.2); 3.852(0.4); 3.329(31.2);2.677(0.4); 2.672(0.5); 2.668(0.4); 2.526(1.3); 2.512(26.5);2.508(53.3); 2.503(70.5); 2.499(52.7); 2.495(27.0); 2.335(0.3);2.330(0.5); 2.325(0.4); 1.990(3.7); 1.397(1.3); 1.299(0.8); 1.259(1.1);1.250(0.4); 1.234(1.6); 1.193(1.2); 1.176(2.1); 1.158(1.1); 0.146(0.6);0.008(4.9); 0.000(120.6); −0.008(6.0); −0.150(0.6) 69 1.74 1.751H-NMR(601.6 MHz, CDCl₃): δ = 9.372(12.3); 8.822(9.3); 8.817(9.2);8.465(7.5); 8.453(8.0); 8.307(16.0); 8.291(8.4); 8.278(8.2); 8.192(1.6);8.154(0.9); 7.937(0.8); 7.910(4.3); 7.898(8.3); 7.885(5.1); 7.837(5.4);7.825(9.3); 7.813(6.0); 7.583(0.8); 7.525(6.1); 7.516(7.8); 7.513(7.9);7.505(6.3); 7.451(9.5); 7.439(8.9); 7.263(66.7); 7.086(0.4); 5.301(4.1);4.129(1.1); 4.112(3.4); 4.094(4.4); 4.072(3.5); 4.055(1.2); 3.882(0.3);3.859(0.5); 3.841(0.4); 3.642(0.4); 3.625(0.5); 3.597(1.4); 3.580(3.6);3.564(4.4); 3.558(4.0); 3.541(3.2); 3.525(1.1); 3.490(0.5);1.577(178.8); 1.426(0.4); 1.371(1.1); 1.333(2.4); 1.285(4.4);1.256(10.6); 1.104(0.5); 0.881(1.6); 0.842(1.6); 0.070(0.6); 0.000(47.7)70 2.82 2.75 1H-NMR(400.0 MHz, d6-DMSO): δ = 9.238(3.7); 8.867(3.7);8.861(4.0); 8.636(9.5); 8.528(1.2); 8.522(1.6); 8.517(1.2); 8.505(1.3);8.500(1.7); 8.494(1.2); 8.175(0.4); 7.395(3.9); 7.389(5.0); 7.366(3.3);7.259(2.5); 7.254(2.4); 7.239(2.0); 7.234(1.9); 7.199(0.4); 5.758(0.4);3.437(0.3); 3.329(65.1); 2.676(0.7); 2.671(1.0); 2.667(0.8); 2.662(0.5);2.541(0.4); 2.525(2.4); 2.511(55.7); 2.507(114.5); 2.502(153.6);2.498(117.2); 2.494(63.2); 2.489(35.6); 2.474(2.6); 2.424(0.4);2.333(1.1); 2.329(1.5); 2.316(16.0); 2.287(0.4); 2.216(1.0); 1.434(0.6);1.296(0.4); 1.234(1.3); 1.073(0.9); 1.055(1.8); 1.038(0.9); 0.700(0.7);0.000(0.3) 71 3.64 3.34 1H-NMR(400.0 MHz, d6-DMSO): δ = 9.238(2.3);9.234(3.8); 8.869(3.7); 8.862(3.9); 8.547(9.3); 8.524(1.2); 8.519(1.5);8.517(1.5); 8.512(1.2); 8.500(1.3); 8.496(1.6); 8.489(1.1); 7.676(5.9);7.360(4.8); 5.754(0.4); 4.038(0.8); 4.033(1.2); 4.021(0.8); 4.007(3.6);3.981(3.7); 3.955(1.3); 3.319(43.7); 2.671(0.4); 2.525(1.1);2.511(20.9); 2.507(41.2); 2.502(53.7); 2.498(39.5); 2.494(19.6);2.410(14.9); 2.329(0.4); 2.080(16.0); 1.989(2.6); 1.398(0.9);1.193(0.7); 1.176(1.4); 1.158(0.7); 0.008(0.8); 0.000(20.9); −0.008(0.8)72 2.35 2.29 1H-NMR(400.0 MHz, d6-DMSO): δ = 9.241(5.8); 8.872(5.8);8.866(6.0); 8.604(14.2); 8.532(1.9); 8.526(2.5); 8.521(1.8); 8.509(2.0);8.504(2.6); 8.498(1.8); 7.944(6.4); 7.934(4.4); 7.496(3.1); 7.470(4.6);5.757(13.7); 4.324(0.6); 4.297(0.7); 4.287(0.7); 4.260(0.7); 4.178(0.6);4.168(0.5); 4.160(0.5); 4.150(1.7); 4.142(1.6); 4.133(0.5); 4.124(1.8);4.115(1.8); 4.105(0.5); 4.097(0.6); 4.087(0.7); 3.970(0.7); 3.943(0.8);3.933(0.6); 3.906(0.6); 3.328(81.6); 2.676(0.5); 2.672(0.7); 2.667(0.5);2.507(83.1); 2.503(109.0); 2.498(81.5); 2.451(12.1); 2.446(15.8);2.408(0.6); 2.333(0.6); 2.329(0.8); 2.325(0.6); 2.189(16.0);2.183(11.7); 2.076(11.2); 0.000(1.0) 73 3.36 3.25 1H-NMR(400.0 MHz,d₆-DMSO): δ = 9.243(3.5); 8.875(3.5); 8.868(3.6); 8.693(7.7);8.535(1.2); 8.530(1.7); 8.524(1.2); 8.512(1.2); 8.507(1.7); 8.501(1.1);7.940(3.1); 7.922(3.1); 7.521(2.7); 7.494(2.7); 4.061(1.2); 4.035(3.8);4.009(3.9); 3.984(1.4); 3.329(53.8); 2.676(0.3); 2.672(0.5); 2.668(0.3);2.507(49.1); 2.503(64.3); 2.499(49.1); 2.471(16.0); 2.414(0.5);2.334(0.3); 2.330(0.4); 2.325(0.3); 2.076(14.3); 1.233(0.9); 0.000(0.4)74 2.34 2.26 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.249(4.3); 9.246(7.4);9.242(4.4); 8.876(7.8); 8.870(8.1); 8.738(16.0); 8.538(2.5); 8.533(3.1);8.531(3.1); 8.527(2.4); 8.515(2.6); 8.510(3.3); 8.503(2.4); 8.447(0.5);8.317(0.7); 8.200(6.2); 8.182(6.2); 7.639(4.3); 7.613(4.3); 5.758(2.5);4.299(0.6); 4.266(1.0); 4.241(0.8); 4.147(0.4); 4.126(0.7); 4.099(0.8);4.038(0.5); 4.020(0.4); 3.568(3.3); 3.329(336.9); 2.676(1.4);2.671(2.0); 2.667(1.5); 2.525(5.0); 2.520(7.9); 2.511(110.1);2.507(225.1); 2.502(308.8); 2.498(233.4); 2.494(111.7); 2.377(1.3);2.334(1.5); 2.329(2.0); 2.325(1.5); 1.989(1.2); 1.234(0.4); 1.207(0.4);1.193(0.6); 1.189(0.7); 1.175(0.8); 1.157(0.3); 0.000(0.9) 75 1.80 1.721H-NMR(400.0 MHz, d6-DMSO): δ = 9.532(12.8); 9.421(6.3); 9.396(0.9);9.367(0.5); 8.619(6.6); 8.449(0.5); 7.792(0.7); 7.772(0.8); 7.525(0.5);7.493(1.2); 7.466(4.3); 7.446(7.2); 7.401(6.7); 7.381(4.2); 7.252(0.3);7.239(0.4); 7.183(0.6); 7.163(0.6); 7.116(0.3); 5.754(1.6); 4.095(0.3);4.077(0.8); 4.060(0.8); 4.041(0.3); 3.865(0.3); 3.846(0.3); 3.318(48.1);2.671(0.9); 2.566(0.8); 2.502(128.3); 2.424(4.2); 2.409(16.0);2.328(1.3); 2.306(0.5); 2.284(2.0); 1.344(0.4); 1.326(0.4); 1.302(0.5);1.285(0.6); 1.265(0.5); 1.248(0.5); 1.242(0.5); 1.225(0.6); 1.205(1.4);1.187(2.1); 1.178(1.2); 1.169(1.3); 1.098(0.4); 0.146(0.6);0.000(109.4); −0.150(0.6) 76 2.88 2.77 1H-NMR(400.0 MHz, d6-DMSO): δ =9.538(16.0); 9.429(7.5); 8.559(8.5); 7.680(4.9); 7.362(3.9); 5.754(1.8);4.034(1.0); 4.008(2.9); 3.982(3.1); 3.956(1.1); 3.318(38.5); 2.671(0.4);2.524(1.0); 2.511(23.9); 2.506(47.7); 2.502(62.3); 2.497(45.4);2.493(22.1); 2.411(12.3); 2.368(0.6); 2.329(0.4); 2.170(0.5);2.080(13.3); 1.352(1.1); 1.336(0.4); 1.259(0.4); 1.250(0.6); 1.229(1.2);0.000(3.8) 77 1.84 1.82 1H-NMR(400.0 MHz, d₆-DMSO): δ = 9.542(16.0);9.429(7.8); 8.612(8.8); 7.949(4.1); 7.939(2.8); 7.497(2.0); 7.471(3.0);5.754(0.9); 4.321(0.4); 4.293(0.5); 4.284(0.5); 4.257(0.5); 4.175(0.4);4.166(0.4); 4.148(1.1); 4.139(1.1); 4.121(1.1); 4.112(1.2); 4.094(0.4);4.085(0.4); 3.969(0.5); 3.942(0.5); 3.932(0.4); 3.905(0.5); 3.317(54.5);2.675(0.5); 2.671(0.7); 2.666(0.5); 2.506(79.6); 2.502(106.3);2.497(82.4); 2.452(8.0); 2.447(10.7); 2.338(0.5); 2.333(0.6);2.328(0.7); 2.324(0.6); 2.258(0.4); 2.188(10.5); 2.182(8.0); 1.234(0.7);0.008(0.5); 0.000(13.1) 78 2.73 2.65 1H-NMR(400.0 MHz, d6-DMSO): δ =9.543(16.0); 9.448(1.1); 9.430(7.6); 9.399(0.4); 9.365(0.8); 8.700(6.9);8.313(0.4); 7.943(2.5); 7.925(2.5); 7.520(2.1); 7.493(2.0); 6.896(0.8);6.706(0.5); 5.753(0.7); 4.364(0.5); 4.346(0.6); 4.058(1.0); 4.032(3.1);4.006(3.2); 3.981(1.2); 3.974(0.6); 3.317(53.6); 2.675(0.6); 2.671(0.8);2.666(0.6); 2.538(0.6); 2.524(2.2); 2.519(3.5); 2.511(44.1);2.506(91.2); 2.502(121.8); 2.497(89.5); 2.493(43.8); 2.473(12.9);2.415(0.6); 2.333(0.6); 2.329(0.8); 2.324(0.6); 1.352(7.8); 1.336(2.3);1.322(1.5); 1.315(0.6); 1.304(0.9); 1.298(1.5); 1.259(2.2); 1.250(3.5);1.229(7.3); 1.180(0.4); 0.868(0.3); 0.851(0.8); 0.834(0.3); 0.008(0.4);0.000(12.0); −0.008 (0.4) 79 2.20 2.17 1H-NMR(400.0 MHz, d6-DMSO): δ =9.302(2.4); 9.298(2.4); 9.296(2.3); 8.849(7.4); 8.813(1.9); 8.809(2.1);8.801(2.1); 8.797(2.1); 8.511(1.1); 8.507(1.5); 8.506(1.4); 8.501(1.2);8.491(1.2); 8.487(1.5); 8.485(1.6); 8.481(1.2); 7.658(1.4); 7.657(1.5);7.646(1.4); 7.645(1.4); 7.638(1.4); 7.637(1.4); 7.626(1.4); 7.625(1.4);7.271(1.0); 7.252(2.8); 7.233(2.2); 7.209(2.7); 7.184(2.0); 7.164(1.2);7.134(1.7); 7.115(1.5); 7.030(0.5); 5.232(8.1); 4.363(0.3); 4.348(0.3);3.329(63.9); 2.672(0.5); 2.668(0.3); 2.543(1.8); 2.526(0.9);2.512(24.0); 2.508(49.4); 2.503(66.3); 2.499(49.7); 2.494(25.0);2.334(0.3); 2.330(0.5); 2.325(0.3); 2.288(16.0); 0.000(0.4) 80 2.39 2.421H-NMR(400.0 MHz, d6-DMSO): δ = 9.307(2.7); 8.818(2.1); 8.808(2.0);8.506(1.8); 8.486(1.8); 7.669(1.5); 7.657(1.7); 7.649(1.6); 7.637(1.4);7.270(1.2); 7.251(2.7); 7.232(1.7); 7.124(2.2); 7.106(1.7); 7.048(3.5);7.014(2.1); 6.995(1.8); 5.390(6.4); 3.329(45.5); 2.672(0.8);2.564(16.0); 2.503(112.3); 2.330(0.9); 2.281(14.1); 1.398(0.4);0.000(18.3) 81 2.17 2.13 1H-NMR(400.0 MHz, d6-DMSO): δ = 9.895(0.4);9.305(5.1); 9.300(5.1); 9.276(0.3); 9.215(0.6); 8.956(0.7); 8.940(0.8);8.871(12.3); 8.815(4.1); 8.811(4.4); 8.803(4.3); 8.799(4.1); 8.514(2.4);8.509(3.3); 8.504(2.5); 8.494(2.6); 8.489(3.4); 8.484(2.4); 8.362(0.4);8.150(0.5); 7.659(3.0); 7.647(3.1); 7.640(3.1); 7.627(2.8); 7.481(0.6);7.461(0.9); 7.446(2.4); 7.438(1.3); 7.425(6.7); 7.406(3.8); 7.385(0.5);7.363(0.3); 7.294(0.5); 7.266(4.8); 7.247(10.3); 7.238(9.9); 7.215(0.9);7.202(0.7); 7.143(3.5); 7.138(3.6); 7.120(3.6); 7.099(0.9); 7.069(1.1);7.053(3.7); 7.030(0.4); 5.286(16.0); 4.789(0.4); 4.770(0.4); 4.583(0.6);4.570(0.6); 4.327(0.8); 4.311(0.7); 4.198(0.5); 4.181(0.5); 3.329(67.5);2.945(1.8); 2.785(1.5); 2.672(1.0); 2.508(109.0); 2.504(135.0);2.499(106.7); 2.330(1.0); 2.288(2.1); 2.076(1.3); 1.959(1.5);1.630(0.5); 1.612(1.0); 1.594(0.5); 1.248(0.7); 1.231(1.3); 1.213(0.6);0.146(0.6); 0.000(110.1); −0.150 (0.6) 82 1.91 1.90 1H-NMR(400.0 MHz,d6-DMSO): δ = 9.296(1.8); 9.291(1.7); 8.862(4.8); 8.809(1.3);8.805(1.4); 8.797(1.4); 8.794(1.3); 8.505(0.9); 8.500(1.2); 8.495(0.8);8.485(0.9); 8.480(1.2); 8.475(0.8); 7.653(1.1); 7.641(1.1); 7.633(1.1);7.621(1.0); 7.391(3.4); 7.369(3.6); 6.940(0.8); 6.933(4.0); 6.911(3.6);5.193(6.3); 3.750(0.9); 3.728(16.0); 3.331(54.2); 2.508(36.4);2.503(46.4); 2.499(35.6); 2.330(0.3); 2.287(0.7); 1.397(0.6); 1.183(0.3)83 2.27 2.27 1H-NMR(400.0 MHz, d6-DMSO): δ = 9.310(3.1); 9.306(3.1);8.817(2.4); 8.808(2.4); 8.781(5.0); 8.525(1.9); 8.505(2.0); 7.673(1.6);7.660(1.8); 7.653(1.8); 7.641(1.5); 7.481(1.4); 7.461(1.6); 7.243(1.3);7.223(2.6); 7.203(1.5); 7.119(1.6); 7.099(1.6); 7.083(2.2); 7.054(2.1);7.009(2.5); 6.990(2.1); 5.271(8.3); 4.109(1.6); 2.672(0.7);2.503(100.4); 2.329(1.0); 2.295(16.0); 0.146(0.3); 0.000(64.6);−0.150(0.4) 84 0.90 1H-NMR(600.1 MHz, d6-DMSO): δ = 9.317(4.7);9.314(4.5); 9.313(4.4); 8.941(0.8); 8.927(0.7); 8.821(3.7); 8.819(3.9);8.813(3.9); 8.810(3.9); 8.794(13.9); 8.788(14.8); 8.785(15.5);8.521(2.1); 8.518(2.7); 8.517(2.7); 8.514(2.1); 8.508(2.2); 8.505(2.7);8.504(2.9); 8.501(2.1); 7.664(2.6); 7.663(2.6); 7.656(2.6); 7.655(2.6);7.651(2.6); 7.649(2.6); 7.643(2.5); 7.641(2.5); 7.468(2.9); 7.460(5.5);7.452(2.8); 5.513(16.0); 4.987(0.4); 4.973(0.4); 4.966(0.4); 4.952(0.4);3.325(57.1); 3.256(0.3); 3.085(2.2); 3.075(0.4); 2.788(2.2); 2.524(0.7);2.521(0.9); 2.518(1.0); 2.509(17.5); 2.506(35.7); 2.503(48.2);2.500(35.3); 2.498(16.9); 2.076(1.3); 1.352(0.6); 1.232(1.0);1.225(0.7); 0.000(0.8) 85 0.90 1.00 1H-NMR(400.0 MHz, d6-DMSO): δ =9.306(5.5); 8.832(9.0); 8.817(14.8); 8.696(0.4); 8.685(0.4); 8.587(7.8);8.571(7.3); 8.513(3.8); 8.493(3.8); 8.317(0.3); 7.663(3.2); 7.650(3.5);7.643(3.5); 7.631(2.9); 5.758(1.0); 5.481(16.0); 3.327(92.7);2.808(0.3); 2.785(0.3); 2.672(2.6); 2.502(293.6); 2.329(2.1);2.288(0.5); 1.990(0.5); 1.397(1.9); 1.175(0.4); 1.150(0.4); 0.146(1.2);0.000(186.4); −0.084 (0.5); −0.150(1.1) 86 1.01 1.07 1H-NMR(400.0 MHz,d6-DMSO): δ = 9.307(1.7); 9.303(1.7); 8.817(1.4); 8.814(1.5);8.805(1.4); 8.802(1.5); 8.701(5.3); 8.519(0.8); 8.514(1.0); 8.509(0.8);8.498(0.9); 8.493(1.1); 8.489(0.8); 7.941(4.3); 7.661(1.0); 7.660(1.0);7.647(1.0); 7.641(1.0); 7.640(1.0); 7.629(0.9); 7.627(0.9); 6.445(0.4);6.427(1.4); 6.409(1.4); 6.392(0.4); 5.758(1.5); 3.895(16.0);3.329(46.3); 2.672(0.4); 2.542(1.1); 2.525(1.0); 2.512(22.5);2.507(45.6); 2.503(60.2); 2.498(44.0); 2.494(21.6); 2.330(0.4);1.890(4.9); 1.872(4.9); 0.000(1.4)

BIOLOGICAL EXAMPLES

Boophilus microplus—Injection Test

Solvent: dimethyl sulphoxide

To produce a suitable preparation of active compound, 10 mg of activecompound are mixed with 0.5 ml of solvent and the concentrate is dilutedwith solvent to the desired concentration.

1 μl of the active compound solution is injected into the abdomen of 5engorged adult female cattle ticks (Boophilus microplus). The animalsare transferred into dishes and kept in a climate-controlled room.

Efficacy is assessed after 7 days by laying of fertile eggs. Eggs whichare not visibly fertile are stored in a climate-controlled cabinet untilthe larvae hatch after about 42 days. An efficacy of 100% means thatnone of the ticks has laid any fertile eggs; 0% means that all the eggsare fertile.

In this test, for example, the following compound from the preparationexamples showed an efficacy of 100% at an application rate of 20μg/animal: 57

Meloidogyne Incognita Test

Solvent: 125.0 parts by weight of acetone

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and theconcentrate is diluted with water to the desired concentration.

Vessels are filled with sand, active compound solution, an egg/larvaesuspension of the southern root-knot nematode (Meloidogyne incognita)and lettuce seeds. The lettuce seeds germinate and the plants develop.The galls develop on the roots.

After 14 days, the nematicidal efficacy in % is determined by theformation of galls. 100% means that no galls were found; 0% means thatthe number of galls on the treated plants corresponds to the untreatedcontrol.

In this test, for example, the following compound from the preparationexamples showed an efficacy of 90% at an application rate of 20 ppm: 63

Myzus persicae—Spray Test

Solvent: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the stated parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of Chinese cabbage leaves (Brassica pekinensis) infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive compound preparation of the desired concentration.

After 6 days, the efficacy in % is determined 100% means that all theaphids have been killed; 0% means that none of the aphids have beenkilled.

In this test, for example, the following compounds from the preparationexamples showed an efficacy of 100% at an application rate of 500 g/ha:1, 2, 3, 4, 5, 7, 9, 15, 20, 23, 34, 35, 39, 40, 43, 45, 48, 49, 50, 51,54, 57, 60, 61, 64, 66, 70, 77, 83, 84

In this test, for example, the following compounds from the preparationexamples showed an efficacy of 90% at an application rate of 500 g/ha:6, 8, 12, 13, 14, 16, 17, 18, 21, 22, 24, 25, 26, 27, 36, 37, 41, 46,47, 52, 53, 55, 56, 58, 59, 62, 63, 67, 71, 72, 73, 74, 76, 78, 80, 81,86

In this test, for example, the following compounds from the preparationexamples showed an efficacy of 90% at an application rate of 100 g/ha:19, 79

Phaedon cochleariae—Spray Test

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the stated parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed withan active compound preparation of the desired concentration and, afterdrying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After 7 days, the efficacy in % is determined 100% means that all thebeetle larvae have been killed; 0% means that no beetle larvae have beenkilled.

In this test, for example, the following compounds from the preparationexamples showed an efficacy of 100% at an application rate of 500 g/ha:11, 37, 62

Spodoptera frugiperda—Spray Test

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the stated parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Leaf discs of maize (Zea mays) are sprayed with an active compoundpreparation of the desired concentration and, after drying, populatedwith caterpillars of the armyworm (Spodoptera frugiperda).

After 7 days, the efficacy in % is determined 100% means that all thecaterpillars have been killed; 0% means that no caterpillars have beenkilled.

In this test, for example, the following compounds from the preparationexamples showed an efficacy of 100% at an application rate of 500 g/ha:11, 37

Tetranychus urticae—Spray Test, OP-Resistant

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the stated parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water.

Discs of bean leaves (Phaseolus vulgaris) infested with all stages ofthe greenhouse red spider mite (Tetranychus urticae) are sprayed with anactive compound preparation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all thespider mites have been killed; 0% means that none of the spider miteshave been killed.

In this test, for example, the following compounds from the preparationexamples showed an efficacy of 90% at an application rate of 500 g/ha:11, 57

Myzus persicae—Spray Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is dissolved using the stated parts by weight ofsolvent and made up with water containing an emulsifier concentration of1000 ppm until the desired concentration is attained. To produce furthertest concentrations, the preparation is diluted withemulsifier-containing water. If the addition of ammonium salts or/andpenetrants is required, these are each added in a concentration of 1000ppm to the preparation solution.

Bell pepper plants (Capsicum annuum) severely infested with the greenpeach aphid (Myzus persicae) are treated by spraying with the activecompound preparation in the desired concentration.

After 6 days, the kill in % is determined 100% means that all the aphidshave been killed; 0% means that no aphids have been killed.

In this test, for example, the following compound from the preparationexamples showed an efficacy of 100% at an application rate of 4 ppm: 44

In this test, for example, the following compound from the preparationexamples showed an efficacy of 96% at an application rate of 4 ppm: 10

The invention claimed is:
 1. A compound of formula (I)

wherein Het represents a radical from the group consisting of

where the dotted line represents the bond to the carbon atom in theN═C-A group attached to Het and G¹ represents N or C-A¹, A¹ representshydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy orin each case optionally substituted cycloalkyl or cycloalkenyl, A²represents hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy,haloalkoxy or in each case optionally substituted cycloalkyl orcycloalkenyl, T represents oxygen or an electron pair, R² representshydrogen, alkyl, haloalkyl or optionally substituted cycloalkyl, R¹represents a radical from the group consisting of hydrogen, alkyl,haloalkyl, cyanoalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl,alkoxy, haloalkoxy, optionally halogen-substituted alkoxyalkyl,optionally halogen-substituted bis(alkoxy)alkyl, optionallyhalogen-substituted alkylsulphanylalkyl, optionally halogen-substitutedalkylcarbonylalkyl, optionally halogen-substituted alkylsulphinylalkyl,optionally halogen-substituted alkylsulphonylalkyl,dialkylaminosulphanylalkyl, dialkylaminosulphinylalkyl,dialkylaminosulphonylalkyl, optionally halogen-substitutedalkoxycarbonyl, optionally halogen-substituted alkoxycarbonylalkyl,optionally halogen-substituted alkynyloxy, optionallyhalogen-substituted alkynyloxycarbonyl, dialkylaminocarbonyl,N-alkyl-N-cycloalkylaminocarbonyl, dialkylaminocarbonylalkyl,N-alkyl-N-cycloalkylaminocarbonylalkyl, heterocyclylcarbonylalkyl,alkylsulphanyl, haloalkylsulphanyl, alkylsulphinyl, haloalkylsulphinyl,alkylsulphonyl, haloalkylsulphonyl, optionally halogen-, cyano-, nitro-,alkyl-, cycloalkyl-, haloalkyl-, alkoxy-, haloalkoxy-, alkoxycarbonyl-,haloalkoxycarbonyl- or hetaryl- (which for its part may optionally bealkyl- or halogen-substituted) substituted cycloalkyl, optionallyhalogen-, cyano-, nitro-, alkyl-, haloalkyl-, cycloalkyl-, alkoxy-,haloalkoxy-, alkoxycarbonyl-, haloalkoxycarbonyl- or hetaryl- (which forits part may optionally be alkyl- or halogen-substituted) substitutedcycloalkylcarbonyl, optionally halogen-, cyano-, nitro-, alkyl-,haloalkyl-, cycloalkyl-, alkoxy-, haloalkoxy-, alkoxycarbonyl-,haloalkoxycarbonyl- or hetaryl- (which for its part may optionally bealkyl- or halogen-substituted) substituted cycloalkylalkyl, optionallysubstituted heterocyclyl, optionally halogen-, cyano- (also in the alkylpart), nitro-, hydroxy-, alkyl-, haloalkyl-, cycloalkyl- (which isoptionally substituted), alkoxy-, haloalkoxy-, alkylthio-,haloalkylthio-, alkylsulphinyl-, alkylsulphonyl-, haloalkylsulphinyl-,haloalkylsulphonyl-, amino-, alkylamino-, dialkylamino-,alkylcarbonylamino-, alkoxycarbonylamino-, alkoxyalkyl-,haloalkoxyalkyl-, alkenyl-, alkynyl-, cycloalkylalkyl-, alkylcarbonyl-,alkoxycarbonyl- or aminocarbonyl-substituted heterocyclylalkyl,optionally halogen-, cyano-, nitro-, hydroxy-, amino-, alkyl-,haloalkyl-, cycloalkyl- (which is optionally substituted) alkoxy- orhaloalkoxy-substituted aryl, optionally halogen-, cyano-(also in thealkyl part), nitro-, hydroxy-, amino-, alkyl-, cycloalkyl- (which isoptionally substituted), haloalkyl-, alkoxy- or haloalkoxy-substitutedarylalkyl, optionally halogen-, cyano-, nitro-, hydroxy-, alkyl-,haloalkyl-, cycloalkyl- (which is optionally substituted), alkoxy-,haloalkoxy-, alkylthio-, haloalkylthio-, alkylsulphinyl-,alkylsulphonyl-, haloalkylsulphinyl-, haloalkylsulphonyl-, amino-,alkylamino-, dialkylamino-, alkylaminocarbonyl-, dialkylaminocarbonyl-,alkylcarbonylamino-, alkoxycarbonylamino-, alkoxyalkyl-,haloalkoxyalkyl-, alkenyl-, alkynyl-, cycloalkylalkyl-, alkylcarbonyl-,alkoxycarbonyl- or aminocarbonyl-substituted hetaryl, optionallyhalogen-, cyano- (also in the alkyl part), nitro-, hydroxy-, alkyl-,haloalkyl-, cycloalkyl- (which is optionally substituted), alkoxy-,haloalkoxy-, alkylthio-, haloalkylthio-, alkylsulphinyl-,alkylsulphonyl-, haloalkylsulphinyl-, haloalkylsulphonyl-, amino-,alkylamino-, dialkylamino-, alkylcarbonylamino-, alkoxycarbonylamino-,alkoxyalkyl-, haloalkoxyalkyl-, alkenyl-, alkynyl-, cycloalkylalkyl-,alkylcarbonyl-, alkoxycarbonyl- or aminocarbonyl-substitutedhetarylalkyl, or R¹ represents a radical from the group consisting of

in which the bond to the nitrogen atom in the C(═V)—N-Q group in formula(I) is marked by the asterisk (*), R represents NR⁷R⁸, or represents anin each case optionally substituted radical from the group consisting ofalkyl, alkenyl, alkynyl, alkoxyalkyl, alkyl-S(O)_(m)-alkyl, R⁷—CO-alkyl,NR⁷R⁸—CO-alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl,cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, phenyl, phenylalkyl,hetaryl and hetarylalkyl, W represents a radical from the groupconsisting of O, S, SO and SO₂, X represents a radical from the groupconsisting of hydrogen, halogen, cyano, nitro, alkyl, haloalkyl, alkoxy,haloalkoxy and cycloalkyl, Y represents a radical from the groupconsisting of hydrogen, halogen, alkyl, cycloalkyl, haloalkyl, alkoxy,haloalkoxy, cyano and NR⁵R⁶, A represents oxygen or sulphur, Qrepresents nitrogen or C—R³ in which R³ represents a radical from thegroup consisting of hydrogen, alkyl, cycloalkyl, haloalkyl, OH, alkoxy,haloalkoxy, SH, alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, NH₂,alkylamino and dialkylamino, V represents a radical from the groupconsisting of oxygen, sulphur and NR⁴, R⁴ represents a radical from thegroup consisting of hydrogen, cyano, alkyl, haloalkyl and cycloalkyl, R⁵represents a radical from the group consisting of hydrogen, alkyl,cycloalkyl and haloalkyl, R⁶ represents a radical from the groupconsisting of hydrogen, alkyl, cycloalkyl and haloalkyl, or R⁵ and R⁶together with the nitrogen to which they are bonded represent anoptionally substituted saturated or unsaturated 3- to 6-membered ringwhich optionally contains one or more further heteroatoms, R⁷ representshydrogen, hydroxy or an in each case optionally substituted radical fromthe group consisting of alkyl, alkoxy, alkoxyalkyl,alkyl-S(O)_(m)-alkyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyl,cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, heterocyclyl,heterocyclylalkyl, phenyl, phenylalkyl, hetaryl and hetarylalkyl, R⁸represents hydrogen, a metal ion, an optionally substituted ammonium ionor an in each case optionally substituted radical from the groupconsisting of alkyl, alkoxy, alkoxyalkyl, alkyl-S(O)_(m)— alkyl and mrepresents a number from the group consisting of 0, 1 and
 2. 2. Acompound of formula (I) according to claim 1, wherein Het represents aradical from the group consisting of

where the dotted line represents the bond to the carbon atom in theN═C-A group attached to Het and G¹ represents N or C-A¹, A¹ represents aradical from the group consisting of hydrogen, halogen, C₁-C₆-alkyl andC₁-C₄-haloalkyl, A² represents a radical from the group consisting ofhydrogen, halogen, C₁-C₆-alkyl and C₁-C₄-haloalkyl, T represents oxygenor an electron pair, R² represents a radical from the group consistingof hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl and C₃-C₆-cycloalkyl which isoptionally mono- to trisubstituted by halogen, cyano, nitro,C₁-C₃-alkyl, C₁-C₃-alkoxy and monosubstituted by C₃-C₆-cycloalkyl, R¹represents a radical from the group consisting of hydrogen, C₁-C₆-alkyl,C₂-C₆-haloalkyl, cyano-C₁-C₆-alkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,optionally halogen-substituted C₁-C₆-alkoxy-C₁-C₆-alkyl, optionallyhalogen-substituted bis(C₁-C₆-alkoxy)-C₁-C₆-alkyl, optionallyhalogen-substituted C₁-C₆-alkylsulphanyl-C₁-C₆-alkyl, optionallyhalogen-substituted C₁-C₄-alkylcarbonyl-C₁-C₄-alkyl, optionallyhalogen-substituted C₁-C₆-alkylsulphinyl-C₁-C₆-alkyl, optionallyhalogen-substituted C₁-C₆-alkylsulphonyl-C₁-C₆-alkyl,di-(C₁-C₆-alkyl)-aminosulphanyl-C₁-C₆-alkyl,di-(C₁-C₆)-alkylaminosulphinyl-C₁-C₆-alkyl,di-(C₁-C₆-alkyl)-aminosulphonyl-C₁-C₆-alkyl, optionallyhalogen-substituted C₁-C₆-alkoxycarbonyl, optionally halogen-substitutedC₁-C₆-alkoxycarbonyl-C₁-C₆-alkyl, optionally halogen-substitutedC₂-C₄-alkynyloxy, optionally halogen-substitutedC₂-C₄-alkynyloxycarbonyl, di-(C₁-C₆-alkyl)-aminocarbonyl,N—C₁-C₆-alkyl-N—C₃-C₆-cycloalkylaminocarbonyl,di-(C₁-C₆-alkyl)-aminocarbonyl-C₁-C₆-alkyl,N—C₁-C₆-alkyl-N—C₃-C₆-cycloalkylaminocarbonyl-C₁-C₆-alkyl,heterocyclylcarbonyl-C₁-C₆-alkyl, C₁-C₆-alkylsulphanyl,C₁-C₆-haloalkylsulphanyl, C₁-C₆-alkylsulphinyl,C₁-C₆-haloalkylsulphinyl, C₁-C₆-alkylsulphonyl,C₁-C₆-haloalkylsulphonyl, optionally halogen-, cyano-, nitro-,C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl-, C₁-C₆-alkoxy-,C₁-C₆-haloalkoxy-, C₁-C₆-alkoxycarbonyl-, C₁-C₆-haloalkoxycarbonyl- orhetaryl- (which for its part is optionally C₁-C₆-alkyl- orhalogen-substituted) substituted C₃-C₆-cycloalkyl, optionally halogen-,cyano-, nitro-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl-,C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-, C₁-C₆-alkoxycarbonyl-,C₁-C₆-haloalkoxycarbonyl- or hetaryl- (which for its part is optionallyC₁-C₆-alkyl- or halogen-substituted) substitutedC₃-C₆-cycloalkylcarbonyl, optionally halogen-, cyano-, nitro-,C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl-, C₁-C₆-alkoxy-,C₁-C₆-haloalkoxy-, C₁-C₆-alkoxycarbonyl-, C₁-C₆-haloalkoxycarbonyl- orhetaryl- (which for its part is optionally C₁-C₆-alkyl- orhalogen-substituted) substituted C₃-C₆-cycloalkyl-C₁-C₆-alkyl,optionally halogen-, cyano- (also in the C₁-C₆-alkyl part ofheterocyclyl-C₁-C₆-alkyl), nitro-, hydroxy-, C₁-C₆-alkyl-,C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl- (which is optionally substituted byhalogen, cyano, C₁-C₆-alkyl and C₃-C₆-cycloalkyl), C₁-C₆-alkoxy-,C₁-C₆-haloalkoxy-, C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio-,C₁-C₆-alkylsulphinyl-, C₁-C₆-alkylsulphonyl-, C₁-C₆-haloalkylsulphinyl-,C₁-C₆-haloalkylsulphonyl-, amino-, C₁-C₆-alkylamino-,di-(C₁-C₆-alkyl)-amino-, C₁-C₆-alkylcarbonylamino-,C₁-C₆-alkoxycarbonylamino-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,C₁-C₆-haloalkoxy-C₁-C₆-alkyl-, C₂-C₆-alkenyl-, C₂-C₆-alkynyl-,C₃-C₆-cycloalkyl-C₁-C₆-alkyl-, C₁-C₆-alkylcarbonyl-,C₁-C₆-alkoxycarbonyl- or aminocarbonyl-substitutedheterocyclyl-C₁-C₆-alkyl, optionally halogen-, cyano-, nitro-, hydroxy-,amino-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl- (which isoptionally substituted by halogen, cyano, C₁-C₆-alkyl andC₃-C₆-cycloalkyl), C₁-C₆-alkoxy- or C₁-C₆-haloalkoxy-substituted aryl,optionally halogen-, cyano- (also in the C₁-C₆-alkyl part ofaryl-C₁-C₆-alkyl), nitro-, hydroxy-, amino-, C₁-C₆-alkyl-,C₁-C₆-haloalkyl-, C₃-C₆-cycloalkyl- (which is optionally substituted byhalogen, cyano, C₁-C₆-alkyl and C₃-C₆-cycloalkyl), C₁-C₆-alkoxy- orC₁-C₆-haloalkoxy-substituted aryl-C₁-C₆-alkyl, optionally halogen-,cyano-, nitro-, hydroxy-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-,C₃-C₆-cycloalkyl- (which is optionally substituted by halogen, cyano,C₁-C₆-alkyl and C₃-C₆-cycloalkyl), C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-,C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio-, C₁-C₆-alkylsulphinyl-,C₁-C₆-alkylsulphonyl-, C₁-C₆-haloalkylsulphinyl-,C₁-C₆-haloalkylsulphonyl-, amino-, C₁-C₆-alkylamino-,di-(C₁-C₆-alkyl)-amino-, C₁-C₆-alkylcarbonylamino-,C₁-C₆-alkylaminocarbonyl-, di-(C₁-C₆-alkyl)-aminocarbonyl-,C₁-C₆-alkoxycarbonylamino-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,C₁-C₆-haloalkoxy-C₁-C₆-alkyl-, C₂-C₆-alkenyl-, C₂-C₆-alkynyl-,C₃-C₆-cycloalkyl-C₁-C₆-alkyl-, C₁-C₆-alkylcarbonyl-,C₁-C₆-alkoxycarbonyl- or aminocarbonyl-substituted hetaryl, optionallyhalogen-, cyano- (also in the C₁-C₆-alkyl part of hetaryl-C₁-C₆-alkyl),nitro-, hydroxy-, C₁-C₆-alkyl-, C₁-C₆-haloalkyl-,C₃-C₆-cycloalkyl-(which is optionally substituted by halogen, cyano,C₁-C₆-alkyl and C₃-C₆-cycloalkyl), C₁-C₆-alkoxy-, C₁-C₆-haloalkoxy-,C₁-C₆-alkylthio-, C₁-C₆-haloalkylthio-, C₁-C₆-alkylsulphinyl-,C₁-C₆-alkylsulphonyl-, C₁-C₆-haloalkylsulphinyl-,C₁-C₆-haloalkylsulphonyl-, amino-, C₁-C₆-alkylamino-,di-(C₁-C₆-alkyl)-amino-, C₁-C₆-alkylcarbonylamino-,C₁-C₆-alkoxycarbonylamino-, C₁-C₆-alkoxy-C₁-C₆-alkyl-,C₁-C₆-haloalkoxy-C₁-C₆-alkyl-, C₂-C₆-alkenyl-, C₂-C₆-alkynyl-,C₃-C₆-cycloalkyl-C₁-C₆-alkyl-, C₁-C₆-alkylcarbonyl-,C₁-C₆-alkoxycarbonyl- or aminocarbonyl-substituted hetaryl-C₁-C₆-alkyl,or R¹ represents a radical from the group consisting of

in which the bond to the nitrogen atom in the C(═V)—N—Q group in formula(I) is marked by the asterisk (*), R represents NR⁷R⁸ or represents ineach case optionally halogen-, oxygen- (leads to C═O) orcyano-substituted C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkyl-S(O)_(m)—C₁-C₄-alkyl, representsR⁷—CO—C₁-C₄-alkyl, represents NR⁷R⁸—CO—C₁-C₄-alkyl, representsC₃-C₆-cycloalkyl which is optionally mono- or disubstituted by oxygen(leads to C═O), C₁-C₄-alkyl, C₃-C₈-cycloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkyl, represents C₃-C₈-cycloalkenyl which is optionally mono-or disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl, representsC₃-C₆-cycloalkyl-C₁-C₄-alkyl which is optionally mono- or disubstitutedby oxygen (leads to C═O), C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxyand C₁-C₄-haloalkyl, represents C₃-C₆-cycloalkenyl-C₁-C₄-alkyl which isoptionally mono- or disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl, representsheterocyclyl which is optionally mono- or disubstituted by oxygen (leadsto C═O), C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkyl, represents heterocyclyl-C₁-C₄-alkyl which is optionallymono- or disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkyl or represents phenyl,phenyl-C₁-C₄-alkyl, hetaryl or hetaryl-C₁-C₄-alkyl, each of which isoptionally mono- to trisubstituted by halogen, cyano, C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, Wrepresents a radical from the group consisting of O, S, SO and SO₂, Xrepresents a radical from the group consisting of hydrogen, halogen,cyano, nitro, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy and C₁-C₆-haloalkoxy, Y represents a radical from the groupconsisting of hydrogen, halogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, cyano and NR⁵R⁶, Arepresents sulphur, Q represents nitrogen or C—R³, R³ represents aradical from the group consisting of hydrogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, OH, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,SH, C₁-C₆-alkylsulphanyl, C₁-C₆-alkylsulphinyl, C₁-C₆-alkylsulphonyl,NH₂, C₁-C₆-alkylamino and di-(C₁-C₆-alkyl)-amino, V represents a radicalfrom the group consisting of oxygen, sulphur and NR⁴, R⁴ represents aradical from the group consisting of hydrogen, cyano, C₁-C₆-alkyl,C₂-C₆-haloalkyl and C₃-C₆-cycloalkyl, R⁵ represents a radical from thegroup consisting of hydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl andC₂-C₆-haloalkyl, R⁶ represents a radical from the group consisting ofhydrogen, C₁-C₆-alkyl, C₃-C₆-cycloalkyl and C₂-C₆-haloalkyl, R⁵ and R⁶can also together with the nitrogen atom to which they are bondedrepresent a saturated to triunsaturated 3- to 6-membered ring which isoptionally substituted by halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, R⁷ represents a radical from the groupconsisting of hydrogen, hydroxy, and C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkyl-S(O)_(m)—C₁-C₄-alkyl,C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkenyl, C₃-C₆-cycloalkyl-C₁-C₃-alkyl,C₃-C₆-cycloalkenyl-C₁-C₃-alkyl, heterocyclyl, heterocyclyl-C₁-C₃-alkyl,each of which is optionally mono- or polysubstituted by halogen or mono-or disubstituted by cyano, and represents phenyl, phenyl-C₁-C₃-alkyl,hetaryl and hetaryl-C₁-C₃-alkyl, each of which is optionally mono- totetrasubstituted by C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₃-C₆-cycloalkyl, halogen or cyano, R⁸ representshydrogen, an alkali or alkaline earth metal ion, or represents anammonium ion which is optionally mono- to tetrasubstituted byC₁-C₄-alkyl, or represents a radical from the group consisting ofC₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl andC₁-C₄-alkyl-S(O)_(m)—C₁-C₄-alkyl, each of which is optionally mono- orpolysubstituted by halogen or mono- or disubstituted by cyano, mrepresents a number from the group consisting of 0, 1 and 2, and wherealkali metal ion is selected from the group consisting of lithium,sodium, potassium, rubidium, caesium, alkaline earth metal ion isselected from the group consisting of beryllium, magnesium, calcium,strontium, barium, halogen is selected from the group consisting offluorine, chlorine, bromine and iodine, aryl (including as part of alarger unit, for example arylalkyl) is selected from the groupconsisting of phenyl, naphthyl, anthryl, phenanthrenyl, hetaryl(synonymous with heteroaryl, including as part of a larger unit, forexample hetarylalkyl) is selected from the group consisting of furyl,thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl,1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl,pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, benzofuryl, benzoisofuryl, benzothienyl,benzoisothienyl, indolyl, isoindolyl, indazolyl, benzothiazolyl,benzoisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl,2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl, cinnolinyl,phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl,benzotriazinyl, purinyl, pteridinyl and indolizinyl, and heterocyclylrepresents a saturated 4-, 5- or 6-membered ring which contains 1 or 2nitrogen atoms and/or one oxygen atom and/or one sulphur atom.
 3. Acompound of formula (I) according to claim 1, wherein Het represents aradical from the group consisting of

where the dotted line represents the bond to the carbon atom in theN═C-A group attached to Het, G¹ represents N or C-A¹, A¹ represents aradical from the group consisting of hydrogen, halogen, C₁-C₄-alkyl andC₁-C₄-haloalkyl, A² represents a radical from the group consisting ofhydrogen, halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl, T represents oxygenor an electron pair, R¹ represents a radical from the group consistingof hydrogen, C₁-C₄-alkyl, C₂-C₄-haloalkyl, cyano-C₁-C₄-alkyl,C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, optionally halogen-substitutedC₁-C₂-alkoxy-C₁-C₄-alkyl, optionally halogen-substitutedbis(C₁-C₂-alkoxy)-C₁-C₄-alkyl, optionally halogen-substitutedC₁-C₄-alkylsulphanyl-C₁-C₄-alkyl, optionally halogen-substitutedC₁-C₄-alkylcarbonyl-C₁-C₄-alkyl, optionally halogen-substitutedC₁-C₄-alkylsulphinyl-C₁-C₄-alkyl, optionally halogen-substitutedC₁-C₄-alkylsulphonyl-C₁-C₄-alkyl,di-(C₁-C₄-alkyl)-aminosulphanyl-C₁-C₄-alkyl,di-(C₁-C₄-alkyl)-aminosulphinyl-C₁-C₄-alkyl,di-(C₁-C₄-alkyl)-aminosulphonyl-C₁-C₄-alkyl, optionallyhalogen-substituted C₁-C₄-alkoxycarbonyl, optionally halogen-substitutedC₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, optionally halogen-substitutedC₂-C₄-alkynyloxy, optionally halogen-substitutedC₂-C₄-alkynyloxycarbonyl, di-(C₁-C₄-alkyl)-aminocarbonyl,N—C₁-C₄-alkyl-N—C₃-C₆-cycloalkylaminocarbonyl,di-(C₁-C₄-alkyl)-aminocarbonyl-C₁-C₄-alkyl,N—C₁-C₄-alkyl-N—C₃-C₆-cycloalkylaminocarbonyl-C₁-C₄-alkyl,heterocyclylcarbonyl-C₁-C₄-alkyl, C₁-C₄-alkylsulphanyl,C₁-C₄-haloalkylsulphanyl, C₁-C₄-alkylsulphinyl,C₁-C₄-haloalkylsulphinyl, C₁-C₄-alkylsulphonyl,C₁-C₄-haloalkylsulphonyl, optionally halogen-, cyano-, nitro-,C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl- C₁-C₄-alkoxy-,C₁-C₄-haloalkoxy-, C₁-C₄-alkoxycarbonyl-, C₁-C₄-haloalkoxycarbonyl- orpyridyl- (which for its part is optionally substituted by C₁-C₄-alkyl orhalogen) substituted C₃-C₆-cycloalkyl, optionally halogen-, cyano-,nitro-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl-C₁-C₄-alkoxy-,C₁-C₄-haloalkoxy-, C₁-C₄-alkoxycarbonyl-, C₁-C₄-haloalkoxycarbonyl- orpyridyl- (which for its part is optionally substituted by C₁-C₄-alkyl orhalogen) substituted C₃-C₆-cycloalkylcarbonyl, optionally halogen-,cyano-, nitro-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-,C₃-C₆-cycloalkyl-C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-,C₁-C₄-alkoxycarbonyl-, C₁-C₄-haloalkoxycarbonyl-, pyridyl-, pyrimidyl-,pyrazanyl-, pyridazinyl-, thiazolyl-, isothiazolyl-, thiadiazolyl-,oxazolyl-, isoxazolyl-, oxadiazolyl-, pyrazolyl-, triazinyl- ortriazolyl- (where the hetaryls mentioned for their part are optionallysubstituted by C₁-C₄-alkyl or halogen) substitutedC₃-C₆-cycloalkyl-C₁-C₄-alkyl, optionally halogen-, cyano- (also in theC₁-C₄-alkyl part of heterocyclyl-C₁-C₄-alkyl), nitro-, hydroxy-,C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl- (which is optionallysubstituted by halogen, cyano, C₁-C₄-alkyl and C₃-C₆-cycloalkyl),C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-,C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulphinyl-, C₁-C₄-alkylsulphonyl-,C₁-C₄-haloalkylsulphinyl-, C₁-C₄-haloalkylsulphonyl-, amino,—C₁-C₄-alkylamino-, di-(C₁-C₄-alkyl)-amino-, C₁-C₄-alkylcarbonylamino-,C₁-C₄-alkoxycarbonylamino-, C₁-C₄-alkoxy-C₁-C₄-alkyl-,C₁-C₄-haloalkoxy-C₁-C₄-alkyl-, C₂-C₄-alkenyl-, C₂-C₄-alkynyl-,C₃-C₆-cycloalkyl-C₁-C₄-alkyl-, C₁-C₄-alkylcarbonyl-,C₁-C₄-alkoxycarbonyl- or aminocarbonyl-substitutedheterocyclyl-C₁-C₄-alkyl, optionally halogen-, cyano-, nitro-, hydroxy-,amino-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl- (which isoptionally substituted by halogen, cyano, C₁-C₄-alkyl andC₃-C₆-cycloalkyl), C₁-C₄-alkoxy- or C₁-C₄-haloalkoxy-substituted aryl,optionally halogen-, cyano- (also in the C₁-C₄-alkyl part ofaryl-C₁-C₄-alkyl), nitro-, hydroxy-, amino-, C₁-C₄-alkyl-,C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl- (which is optionally substituted byhalogen, cyano, C₁-C₄-alkyl and C₃-C₆-cycloalkyl), C₁-C₄-alkoxy- orC₁-C₄-haloalkoxy-substituted aryl-C₁-C₄-alkyl, optionally halogen-,cyano-, nitro-, hydroxy-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-,C₃-C₆-cycloalkyl- (which is optionally substituted by halogen, cyano,C₁-C₄-alkyl and C₃-C₆-cycloalkyl), C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-,C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulphinyl-,C₁-C₄-alkylsulphonyl-, C₁-C₄-haloalkylsulphinyl-,C₁-C₄-haloalkylsulphonyl-, amino-, C₁-C₄-alkylamino-,di-(C₁-C₄-alkyl)-amino-, C₁-C₄-alkylcarbonylamino-,C₁-C₄-alkylaminocarbonyl-, di-(C₁-C₄-alkyl)-aminocarbonyl-,C₁-C₄-alkoxycarbonylamino-, C₁-C₄-alkoxy-C₁-C₄-alkyl-,C₁-C₄-haloalkoxy-C₁-C₄-alkyl-, C₂-C₄-alkenyl-, C₂-C₄-alkynyl-,C₃-C₆-cycloalkyl-C₁-C₄-alkyl-, C₁-C₄-alkylcarbonyl-,C₁-C₄-alkoxycarbonyl- or aminocarbonyl-substituted hetaryl, optionallyhalogen-, cyano- (also in the C₁-C₄-alkyl part of hetaryl-C₁-C₄-alkyl),nitro-, hydroxy-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-, C₃-C₆-cycloalkyl-(which is optionally substituted by halogen, cyano, C₁-C₄-alkyl andC₃-C₆-cycloalkyl), C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-,C₁-C₄-haloalkylthio-, C₁-C₄-alkylsulphinyl-, C₁-C₄-alkylsulphonyl-,C₁-C₄-haloalkylsulphinyl-, C₁-C₄-haloalkylsulphonyl-, amino-,C₁-C₄-alkylamino-, di-(C₁-C₄-alkyl)-amino-, C₁-C₄-alkylcarbonylamino-,C₁-C₄-alkoxycarbonylamino-, C₁-C₄-alkoxy-C₁-C₄-alkyl-,C₁-C₄-haloalkoxy-C₁-C₄-alkyl-, C₂-C₄-alkenyl-, C₂-C₄-alkynyl-,C₃-C₆-cycloalkyl-C₁-C₄-alkyl-, C₁-C₄-alkylcarbonyl-,C₁-C₄-alkoxycarbonyl- or aminocarbonyl-substituted hetaryl-C₁-C₄-alkyl,or R¹ represents a radical from the group consisting of

in which the bond to the nitrogen atom in the C(═V)—N-Q group in formula(I) is marked by the asterisk (*), R represents NR⁷R⁸ or representsC₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₃-alkyl,C₁-C₄-alkyl-S(O)_(m)—C₁-C₃-alkyl, each of which is optionally mono- toheptasubstituted by halogen, mono- or disubstituted by oxygen (leads toC═O) or mono- or disubstituted by cyano, represents R⁷—CO—C₁-C₂-alkyl,represents NR⁷R⁸—CO—C₁-C₂-alkyl, represents C₃-C₈-cycloalkyl which isoptionally mono- or disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkyl, representsC₃-C₈-cycloalkenyl which is optionally mono- or disubstituted by oxygen(leads to C═O), C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkyl, represents C₃-C₆-cycloalkyl-C₁-C₄-alkyl which isoptionally mono- or disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkyl, representsC₃-C₆-cycloalkenyl-C₁-C₄-alkyl which is optionally mono- ordisubstituted by oxygen (leads to C═O), C₁-C₄-alkyl, C₃-C₆-cycloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkyl, represents heterocyclyl which isoptionally mono- or disubstituted by oxygen (leads to C═O), C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkyl, representsheterocyclyl-C₁-C₄-alkyl which is optionally mono- or disubstituted byoxygen (leads to C═O), C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkyl or represents phenyl, phenyl-C₁-C₄-alkyl, hetaryl orhetaryl-C₁-C₄-alkyl, each of which is optionally mono- to trisubstitutedby halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, W represents a radical from the groupconsisting of S, SO and SO₂, X represents a radical from the groupconsisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano,nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy andC₁-C₄-haloalkoxy, Y represents a radical from the group consisting ofhydrogen, fluorine, chlorine, bromine, iodine, cyano, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, Arepresents sulphur, Q represents nitrogen or C—R³, R³ represents aradical from the group consisting of hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₃-C₆-cycloalkyl, OH, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,SH, C₁-C₄-alkylsulphanyl, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,NH₂, C₁-C₄-alkylamino and di-(C₁-C₄-alkyl)-amino, V represents oxygen,R⁷ represents a radical from the group consisting of hydrogen, hydroxy,or C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,C₁-C₄-alkyl-S(O)_(m)—C₁-C₃-alkyl, C₁-C₄-alkylcarbonyl,C₁-C₄-alkoxycarbonyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₃-alkyl,heterocyclyl and heterocyclyl-C₁-C₃-alkyl, each of which is optionallymono- or polysubstituted by halogen or mono- or disubstituted by cyano,or represents phenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl,pyrazolyl, thienyl, furanyl, pyridinylmethyl or thiazolylmethyl, each ofwhich is optionally mono- to trisubstituted by C₁-C₄-alkyl,C₁-C₃-haloalkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, cyclopropyl, fluorine,chlorine, bromine or cyano, R⁸ represents hydrogen, represents an alkalior alkaline earth metal ion, or represents an ammonium ion which isoptionally mono- to tetrasubstituted by C₁-C₄-alkyl, or represents aradical from the group consisting of C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₂-alkyl and C₁-C₄-alkyl-S(O)_(m)—C₁-C₂-alkyl, each ofwhich is optionally mono- or polysubstituted by halogen or mono- ordisubstituted by cyano, m represents a number from the group consistingof 0, 1 and 2, and where alkali metal ion is selected from the groupconsisting of lithium, sodium, potassium, rubidium, caesium, alkalineearth metal ion is selected from the group consisting of beryllium,magnesium, calcium, strontium, barium, halogen is selected from thegroup consisting of fluorine, chlorine, bromine and iodine, aryl(including as part of a larger unit, for example arylalkyl) is selectedfrom the group consisting of phenyl, naphthyl, anthryl andphenanthrenyl, hetaryl (synonymous with heteroaryl, also as part of alarger unit such as, for example, hetarylalkyl) is selected from thegroup consisting of pyrazolyl, imidazolyl, 1,2,3-triazolyl,1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl,pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, benzothienyl, and heterocyclyl is selected from thegroup consisting of azetidinyl, azolidinyl, azinanyl, oxetanyl,oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl,tetrahydrofuryl, piperazinyl, morpholinyl.
 4. A compound of formula (I)according to claim 1, wherein Het is a radical from the group of

where the dotted line represents the bond to the carbon atom in theN═C-A group attached to Het, G¹ represents N or C-A¹, A¹ represents aradical from the group consisting of hydrogen, fluorine and chlorine, Trepresents oxygen or an electron pair, R¹ represents a radical from thegroup consisting of methyl, ethyl, isopropyl, n-propyl, n-butyl,isobutyl, sec-butyl, tert-butyl, 2,2,2-trifluoroethyl,2,2-difluoroethyl, 2,2-difluoro-n-propyl, methylsulphanylmethyl,methylsulphanylethyl, methyl sulphanyl-n-propyl,trifluoromethylsulphonylmethyl, ethylsulphonylmethyl,2,2,2-trifluoroethylsulphonylmethyl, 2,2-difluoroethylsulphonylmethyl,isopropylsulphanylmethyl, methylsulphinylmethyl,trifluoromethylsulphinylmethyl, ethylsulphinylmethyl,2,2,2-trifluoroethylsulphinylmethyl, 2,2-difluoroethylsulphinylmethyl,isopropylsulphinylmethyl, methylsulphonylmethyl,trifluoromethylsulphonylmethyl, ethylsulphonylmethyl,2,2,2-trifluoroethylsulphonylmethyl, 2,2-difluoroethylsulphonylmethyl,isopropylsulphonylmethyl, methoxycarbonyl, ethoxycarbonyl,methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl,ethoxycarbonylethyl, dimethylaminocarbonyl, diethylaminocarbonyl,N-ethyl-N-methylaminocarbonyl, N-isopropyl-N-methylaminocarbonyl,dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl,N-ethyl-N-methylaminocarbonylmethyl,N-isopropyl-N-methylaminocarbonylmethyl, dimethylaminocarbonylethyl,diethylaminocarbonylethyl, N-ethyl-N-methylaminocarbonylethyl,N-isopropyl-N-methylaminocarbonylethyl,N-cyclopropyl-N-methylaminocarbonylmethyl,N-cyclopropyl-N-methylaminocarbonylethyl, methylsulphanyl,trifluoromethylsulphanyl, ethylsulphanyl, 2,2,2-trifluoroethylsulphanyl, 2,2-difluoroethyl sulphanyl, isopropylsulphanyl,methylsulphinyl, trifluoromethylsulphinyl, ethylsulphinyl,2,2,2-trifluoroethylsulphinyl, 2,2-difluoroethylsulphinyl,isopropylsulphinyl, methylsulphonyl, trifluoromethylsulphonyl,ethylsulphonyl, 2,2,2-trifluoroethylsulphonyl,2,2-difluoroethylsulphonyl, isopropylsulphonyl, cyclopropyl,1-cyanocyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl,2-cyanocyclopropyl, 2-chlorocyclopropyl, 2-fluorocyclopropyl,2,2,3,3-tetrafluorocyclopropyl, 2-cyclopropylcyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, 4-trifluoromethylcyclohexyl, cyclopropylmethyl,cyclopropylethyl, cyclobutylmethyl, N-cyclopropyl-N-methylaminocarbonyl,morpholin-4-ylcarbonylmethyl, piperazin-1-ylcarbonylmethyl,4-methylpiperazin-1-ylcarbonylmethyl, of heterocyclylmethyl andheterocyclylethyl, each of which is optionally mono-, di- ortrisubstituted by identical or different substitutents from the groupconsisting of fluorine, chlorine, bromine, cyano, nitro, hydroxy, amino,methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl,methoxy, trifluoromethoxy and difluoromethoxy, of in each casecyclopropyl-substituted heterocyclylmethyl and heterocyclylethyl, wherethe cyclopropyl radical is optionally mono- or disubstituted by methyl,fluorine, chlorine, cyano or monosubstituted by cyclopropyl, of hetarylwhich is optionally mono- or disubstituted by identical or differentsubstituents from the group consisting of fluorine, chlorine, bromine,cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl,trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy,difluoromethoxy, dimethylaminocarbonyl, of hetaryl substituted bycyclopropyl, where the cyclopropyl radical is optionally mono- ordisubstituted by methyl, fluorine, chlorine, cyano or monosubstituted bycyclopropyl, of aryl which is optionally mono-, di- or trisubstituted byidentical or different substituents from the group consisting offluorine, chlorine, bromine, cyano, nitro, hydroxy, amino, methyl,ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy,trifluoromethoxy, difluoromethoxy and trifluoroethoxy, of arylsubstituted by cyclopropyl, where the cyclopropyl radical is optionallymono- or disubstituted by methyl, fluorine, chlorine, cyano ormonosubstituted by cyclopropyl, of arylmethyl and arylethyl, each ofwhich is optionally mono-, di- or trisubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,bromine, cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl,tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy,difluoromethoxy, of arylmethyl and arylethyl in each case substituted bycyclopropyl, where the cyclopropyl radical is optionally mono- ordisubstituted by methyl, fluorine, chlorine, cyano or monosubstituted bycyclopropyl, of hetarylmethyl and hetarylethyl, each of which isoptionally mono- or disubstituted by identical or different substituentsfrom the group consisting of fluorine, chlorine, bromine, cyano, nitro,hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl,difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, ofhetarylmethyl and hetarylethyl in each case substituted by cyclopropyl,where the cyclopropyl radical is optionally mono- or disubstituted bymethyl, fluorine, chlorine, cyano or monosubstituted by cyclopropyl, orR¹ represents a radical from the group consisting of

in which the bond to the nitrogen atom in the C(═V)—N-Q group in formula(I) is marked by the asterisk (*), R represents NR⁷R⁸ or represents aradical from the group consisting of C₁-C₄-alkyl, C₃-C₄-alkenyl,C₃-C₄-alkynyl, C₁-C₂-alkoxy-C₁-C₂-alkyl andC₁-C₂-alkyl-S(O)_(m)—C₁-C₂-alkyl, each of which is optionally mono-,di-, tri-, tetra- or pentasubstituted by fluorine, chlorine or mono- ordisubstituted by cyano, represents R⁷—CO—C₁-C₂-alkyl, representsNR⁷R⁸—CO—C₁-C₂-alkyl, represents C₃-C₆-cycloalkyl which is optionallymono- or disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy or C₁-C₂-haloalkylor by an oxygen atom (leads to C═O), represents C₃-C₆-cycloalkenyl whichis optionally mono- or disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy orC₁-C₂-haloalkyl or by an oxygen atom (leads to C═O), representsC₃-C₆-cycloalkyl-C₁-C₂-alkyl which is optionally mono- or disubstitutedby C₁-C₂-alkyl, C₁-C₂-alkoxy or C₁-C₂-haloalkyl, representsC₃-C₆-cycloalkenyl-C₁-C₂-alkyl which is optionally mono- ordisubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy or C₁-C₂-haloalkyl,represents heterocyclyl which is optionally mono- or disubstituted byC₁-C₂-alkyl, C₁-C₂-alkoxy or C₁-C₂-haloalkyl, representsheterocyclyl-C₁-C₂-alkyl which is optionally mono- or disubstituted byC₁-C₂-alkyl, C₁-C₂-alkoxy or C₁-C₂-haloalkyl or represents phenyl,benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl, thienyl,furanyl, pyridinylmethyl or thiazolylmethyl, each of which is optionallymono- or disubstituted by fluorine, chlorine, bromine, cyano, methyl,ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxyor trifluoromethoxy, W represents a radical from the group consisting ofS, SO and SO₂, X represents a radical from the group consisting ofhydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl,trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy,Y represents a radical from the group consisting of hydrogen, fluorine,chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy,ethoxy, difluoromethoxy and trifluoromethoxy, A represents sulphur, Qrepresents nitrogen or C—R³, R³ represents hydrogen, V representsoxygen, R⁷ represents a radical from the group consisting of hydrogen,hydroxy, or represents C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkyl-S(O)_(m)—C₁-C₂-alkyl,C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxycarbonyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₃-alkyl, heterocyclyl or heterocyclyl-C₁-C₃-alkyl,each of which is optionally mono-, di-, tri-, tetra- or pentasubstitutedby fluorine, chlorine or mono- or disubstituted by cyano, or representsphenyl, benzyl, pyridyl, pyrimidyl, thiazolyl, oxazolyl, pyrazolyl,thienyl, furanyl, pyridinylmethyl or thiazolylmethyl, each of which isoptionally mono- to trisubstituted by C₁-C₄-alkyl, C₁-C₃-haloalkyl,C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, cyclopropyl, fluorine, chlorine, bromineor cyano, R⁸ represents hydrogen, an alkali or alkaline-earth metal ion,an ammonium ion which is optionally mono- to tetrasubstituted byC₁-C₄-alkyl, or represents a radical from the group consisting ofC₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₂-alkyl andC₁-C₄-alkyl-S(O)_(m)—C₁-C₂-alkyl, each of which is optionally mono-,di-, tri-, tetra- or pentasubstituted by fluorine, chlorine or is mono-or disubstituted by cyano, m represents a number from the groupconsisting of 0, 1 and 2, and where alkali metal ion represents an ionfrom the group consisting of lithium, sodium, potassium, rubidium,caesium, alkaline earth metal ion represents an ion from the groupconsisting of beryllium, magnesium, calcium, strontium, barium, halogenrepresents fluorine, chlorine, bromine and iodine, heterocyclylrepresents a radical from the group consisting of oxetanyl, thiethanyl,tetrahydrofuryl and morpholinyl, aryl represents phenyl and hetaryl(synonymous with heteroaryl, including as part of a larger unit such as,for example, hetarylalkyl) represents a radical from the groupconsisting of pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, thiazolyl,pyrazolyl and benzothienyl.
 5. A compound of formula (I) according toclaim 1, wherein Het represents a radical from the group consisting of

where the dotted line represents the bond to the carbon atom in theN═C-A group attached to Het, G¹ represents N or C-A¹, A¹ represents aradical from the group consisting of hydrogen, fluorine and chlorine, Trepresents oxygen or an electron pair, R¹ represents a radical from thegroup consisting of methyl, ethyl, isopropyl, n-propyl, n-butyl,isobutyl, sec-butyl, tert-butyl, 2,2,2-trifluoroethyl,2,2-difluoroethyl, 2,2-difluoro-n-propyl, methylsulphanylmethyl,methylsulphanylethyl, methyl sulphanyl-n-propyl,trifluoromethylsulphonylmethyl, ethylsulphonylmethyl,2,2,2-trifluoroethylsulphonylmethyl, 2,2-difluoroethylsulphonylmethyl,isopropylsulphanylmethyl, methylsulphinylmethyl,trifluoromethylsulphinylmethyl, ethylsulphinylmethyl,2,2,2-trifluoroethylsulphinylmethyl, 2,2-difluoroethylsulphinylmethyl,isopropylsulphinylmethyl, methylsulphonylmethyl,trifluoromethylsulphonylmethyl, ethylsulphonylmethyl,2,2,2-trifluoroethylsulphonylmethyl, 2,2-difluoroethylsulphonylmethyl,isopropylsulphonylmethyl, methoxycarbonyl, ethoxycarbonyl,methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl,ethoxycarbonylethyl, dimethylaminocarbonyl, diethylaminocarbonyl,N-ethyl-N-methylaminocarbonyl, N-isopropyl-N-methylaminocarbonyl,dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl,N-ethyl-N-methylaminocarbonylmethyl,N-isopropyl-N-methylaminocarbonylmethyl, dimethylaminocarbonylethyl,diethylaminocarbonylethyl, N-ethyl-N-methylaminocarbonylethyl,N-isopropyl-N-methylaminocarbonylethyl,N-cyclopropyl-N-methylaminocarbonylmethyl,N-cyclopropyl-N-methylaminocarbonylethyl, methylsulphanyl,trifluoromethylsulphanyl, ethylsulphanyl, 2,2,2-trifluoroethylsulphanyl, 2,2-difluoroethyl sulphanyl, isopropylsulphanyl,methylsulphinyl, trifluoromethylsulphinyl, ethylsulphinyl,2,2,2-trifluoroethylsulphinyl, 2,2-difluoroethylsulphinyl,isopropylsulphinyl, methylsulphonyl, trifluoromethylsulphonyl,ethylsulphonyl, 2,2,2-trifluoroethylsulphonyl,2,2-difluoroethylsulphonyl, isopropylsulphonyl, cyclopropyl,1-cyanocyclopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl,2-cyanocyclopropyl, 2-chlorocyclopropyl, 2-fluorocyclopropyl,2,2,3,3-tetrafluorocyclopropyl, 2-cyclopropylcyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, 4-trifluoromethylcyclohexyl, cyclopropylmethyl,cyclopropylethyl, cyclobutylmethyl, N-cyclopropyl-N-methylaminocarbonyl,morpholin-4-ylcarbonylmethyl, piperazin-1-ylcarbonylmethyl,4-methylpiperazin-1-ylcarbonylmethyl, of heterocyclylmethyl andheterocyclylethyl, each of which is optionally mono-, di- ortrisubstituted by identical or different substitutents from the groupconsisting of fluorine, chlorine, bromine, cyano, nitro, hydroxy, amino,methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl,methoxy, trifluoromethoxy and difluoromethoxy, of in each casecyclopropyl-substituted heterocyclylmethyl and heterocyclylethyl, wherethe cyclopropyl radical is optionally mono- or disubstituted by methyl,fluorine, chlorine, cyano or monosubstituted by cyclopropyl, of hetarylwhich is optionally mono- or disubstituted by identical or differentsubstituents from the group consisting of fluorine, chlorine, bromine,cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl,trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy,difluoromethoxy, dimethylaminocarbonyl, of hetaryl substituted bycyclopropyl, where the cyclopropyl radical is optionally mono- ordisubstituted by methyl, fluorine, chlorine, cyano or monosubstituted bycyclopropyl, of aryl which is optionally mono-, di- or trisubstituted byidentical or different substituents from the group consisting offluorine, chlorine, bromine, cyano, nitro, hydroxy, amino, methyl,ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy,trifluoromethoxy, difluoromethoxy and trifluoroethoxy, of arylsubstituted by cyclopropyl, where the cyclopropyl radical is optionallymono- or disubstituted by methyl, fluorine, chlorine, cyano ormonosubstituted by cyclopropyl, of arylmethyl and arylethyl, each ofwhich is optionally mono-, di- or trisubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,bromine, cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl,tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy,difluoromethoxy, of arylmethyl and arylethyl in each case substituted bycyclopropyl, where the cyclopropyl radical is optionally mono- ordisubstituted by methyl, fluorine, chlorine, cyano or monosubstituted bycyclopropyl, of hetarylmethyl and hetarylethyl, each of which isoptionally mono- or disubstituted by identical or different substituentsfrom the group consisting of fluorine, chlorine, bromine, cyano, nitro,hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl,difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, ofhetarylmethyl and hetarylethyl in each case substituted by cyclopropyl,where the cyclopropyl radical is optionally mono- or disubstituted bymethyl, fluorine, chlorine, cyano or monosubstituted by cyclopropyl, orR¹ represents the radical of the formula

in which the bond to the nitrogen atom in the C(═V)—N-Q group in formula(I) is marked by the asterisk (*), R represents methyl, ethyl, propyl,isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, allyl, 2-butenyl,propargyl, 2-butynyl, each of which is optionally mono-, di- ortrisubstituted by fluorine or monosubstituted by cyano, or representsC₃-C₆-cycloalkyl which is optionally monosubstituted by methyl, ethyl,methoxy, ethoxy or trifluoromethyl, or represents C₃-C₆-cycloalkylmethylwhich is optionally monosubstituted by methyl, ethyl, methoxy ortrifluoromethyl, or represents phenyl, benzyl, pyridyl, pyrimidyl,thiazolyl and pyridinylmethyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, cyano, methyl, ethyl,isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy,difluoromethoxy or trifluoromethoxy, W represents a radical from thegroup consisting of S, SO and SO₂, X represents a radical from the groupconsisting of hydrogen, fluorine, chlorine, bromine, cyano, methyl,ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy andtrifluoromethoxy, Y represents a radical from the group consisting ofhydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl,trifluoromethyl, methoxy, ethoxy, difluoromethoxy and trifluoromethoxy,A represents sulphur, Q represents nitrogen or C—R³, R³ representshydrogen or methyl, V represents oxygen and where alkali metal ionrepresents an ion from the group consisting of lithium, sodium,potassium, rubidium, caesium, alkaline earth metal ion represents an ionfrom the group consisting of beryllium, magnesium, calcium, strontium,barium, halogen represents fluorine, chlorine, bromine and iodine,heterocyclyl represents a radical from the group consisting of oxetanyl,thiethanyl, tetrahydrofuryl and morpholinyl, aryl represents phenyl andhetaryl (synonymous with heteroaryl, including as part of a larger unitsuch as, for example, hetarylalkyl) represents a radical from the groupconsisting of pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, thiazolyl,pyrazolyl and benzothienyl.
 6. A compound of formula (I) according toclaim 1 wherein Het represents

where the dotted line represents the bond to the carbon atom in theN═C-A group attached to Het, G¹ represents C-A¹, A¹ represents hydrogen,T represents oxygen or an electron pair, R¹ represents methyl, ethyl,isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert-butyl,2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2,2-difluoro-n-propyl,dimethylaminocarbonyl, diethylaminocarbonyl,N-ethyl-N-methylaminocarbonyl, N-isopropyl-N-methylaminocarbonyl,dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl,N-ethyl-N-methylaminocarbonylmethyl,N-isopropyl-N-methylaminocarbonylmethyl, dimethylaminocarbonylethyl,diethylaminocarbonylethyl, N-ethyl-N-methylaminocarbonylethyl,N-isopropyl-N-methylaminocarbonylethyl,N-cyclopropyl-N-methylaminocarbonylmethyl,N-cyclopropyl-N-methylaminocarbonylethyl, cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, represents hetarylmethyl or hetarylethyl, eachof which is optionally mono- or disubstituted by identical or differentsubstituents from the group consisting of fluorine, chlorine, bromine,cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl,trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy,difluoromethoxy, R¹ also represents

in which the bond to the nitrogen atom in the C(═V)—N-Q group in formula(I) is marked by the asterisk (*), R represents C₁-C₄-alkyl which isoptionally mono- to trisubstituted by fluorine or chlorine, W representsa radical from the group S and SO, X represents a radical from the groupconsisting of hydrogen, fluorine, chlorine, bromine, methyl, ethyl,difluoromethyl and trifluoromethyl, Y represents a radical from thegroup consisting of hydrogen, fluorine, chlorine, bromine, iodine,methyl and ethyl, A represents sulphur, Q represents nitrogen or C—R³,R³ represents hydrogen, V represents oxygen and where halogen representsfluorine, chlorine, bromine and iodine and hetaryl represents a radicalfrom the group consisting of pyridyl, pyrimidinyl, thiazolyl, pyrazolyland benzothienyl.
 7. A compound of formula (I) according to claim 1wherein Het represents

where the dotted line represents the bond to the carbon atom in theN═C-A group attached to Het, G¹ represents C-A¹ or N, A¹ representshydrogen or fluorine, T represents oxygen or an electron pair, R¹represents methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl,sec-butyl, tert-butyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl,2,2-difluoro-n-propyl, dimethylaminocarbonyl, diethylaminocarbonyl,N-ethyl-N-methylaminocarbonyl, N-isopropyl-N-methylaminocarbonyl,dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl,N-ethyl-N-methylaminocarbonylmethyl,N-isopropyl-N-methylaminocarbonylmethyl, dimethylaminocarbonylethyl,diethylaminocarbonylethyl, N-ethyl-N-methylaminocarbonylethyl,N-isopropyl-N-methylaminocarbonylethyl,N-cyclopropyl-N-methylaminocarbonylmethyl,N-cyclopropyl-N-methylaminocarbonylethyl, cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cyclopropylmethyl, optionallydimethylaminocarbonyl-substituted benzothienyl, optionally halogen-,methyl- or trifluoroethoxy-substituted phenyl, optionally methyl-,methoxy-, difluoromethoxy- or halogen-substituted phenylmethyl,represents hetarylmethyl or hetarylethyl, each of which is optionallymono- or disubstituted by identical or different substituents from thegroup consisting of fluorine, chlorine, bromine, cyano, nitro, hydroxy,amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl,difluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, R¹ alsorepresents

in which the bond to the nitrogen atom in the C(═V)—N-Q group in formula(I) is marked by the asterisk (*), R represents C₁-C₄-alkyl which isoptionally mono- to trisubstituted by fluorine or chlorine, W representsa radical from the group consisting of S, SO and SO₂, X represents aradical from the group consisting of hydrogen, fluorine, chlorine,bromine, methyl, ethyl, difluoromethyl and trifluoromethyl, Y representsa radical from the group consisting of hydrogen, fluorine, chlorine,bromine, iodine, methyl and ethyl, A represents sulphur, Q representsnitrogen or C—R³, R³ represents hydrogen or methyl, V represents oxygenand where halogen represents fluorine, chlorine, bromine and iodine andhetaryl represents a radical from the group consisting of pyridyl,pyrimidinyl, thiazolyl, pyrazolyl and benzothienyl.
 8. A compound offormula (I) according to claim 1 wherein Het represents the radical ofthe formula


9. A compound of formula (I) according to claim 1 wherein T representsan electron pair.
 10. A compound of formula (I) according to claim 1wherein Het represents pyridin-3-yl.
 11. A compound of formula (I)according to claim 1 wherein Het represents 5-fluoropyridin-3-yl.
 12. Acompound of formula (I) according to claim 1 wherein R¹ represents theradical


13. A composition, comprising at least one compound of formula (I)according to claim 1 and one or more customary extenders and/orsurfactants.
 14. A method for controlling an animal pest comprisingapplying one or more compounds of the formula (I) according to claim 1to the pest and/or a habitat thereof.
 15. The compound according toclaim 1, wherein Het represents


16. The compound according to claim 10, wherein A is S; Q is CH; V is O;and R¹ is